KR20200094164A - Microbial thiazole derivatives - Google Patents

Abstract

.Compounds of formula (I):
[Formula I]

.

Description

Microbial thiazole derivatives

The present invention relates to an antimicrobial thiazole derivative, for example as an active ingredient, which has an antimicrobial activity, in particular a fungicidal activity. The present invention also provides the preparation of such thiazole derivatives, agrochemical compositions comprising at least one of the thiazole derivatives, and phytopathogenic microorganisms in plants, harvested edible crops, seeds or non-living materials in agriculture or horticulture. , Preferably relates to the use of a thiazole derivative or composition thereof for controlling or preventing fungal invasion.

WO 2010/012793 describes amino-thiazole derivatives as pesticides.

According to the present invention, there is provided a compound of formula (I): or a salt or N-oxide thereof:

[Formula I]

[In the above formula,

R ¹ is halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ haloalkyl;

R ² is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl;

R ³ is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl;

R ⁴ is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl;

R ⁵ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₆ haloalkenyl, C _2- C ₆ haloalkynyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moieties are nitrogen, oxygen and sulfur A 5 or 6 membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties, respectively, represented by R ⁷ Optionally substituted with 1 to 3 groups;

R ⁶ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₆ haloalkenyl, C _2- C ₆ haloalkynyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moieties are nitrogen, oxygen and sulfur A 5 or 6 membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties, respectively, represented by R ⁷ Optionally substituted with 1 to 3 groups;

R ⁷ is halogen, cyano, hydroxyl, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, or C ₃ -C ₄ cycloalkyl;

X is C-H or N].

Surprisingly, it has been found that the novel compounds of formula (I) have, in practice, a very favorable level of biological activity in protecting plants against diseases caused by fungi.

According to a second aspect of the invention, there is provided a pesticide composition comprising an effective amount of a fungicidal agent according to the invention of the compound of formula (I). Such agricultural compositions may further comprise at least one additional active ingredient and/or agrochemically acceptable diluent or carrier.

According to a third aspect of the present invention, there is provided a method for controlling or preventing the invasion of phytopathogenic microorganisms into useful plants, wherein a fungicidally effective amount of the compound of formula I, or a composition comprising the compound as an active ingredient, is present in the plant. , Applies to parts of it or to its habitat.

According to a fourth aspect of the invention, the use of the compound of formula I as fungicide is provided. According to this particular aspect of the invention, the use may or may not include a method for treatment of the human or animal body by surgery or therapy.

When substituents are indicated as being “optionally substituted”, it means that they may or may not have one or more of the same or different substituents, eg 1, 2, or 3 R ⁷ substituents. For example, C ₁ -C ₆ alkyl substituted with 1, 2 or 3 halogens is -CH ₂ Cl, -CHCl ₂ , -CCl ₃ , -CH ₂ F, -CHF ₂ , -CF ₃ , -CH ₂ CF ₃ or -CF ₂ CH ₃ groups. As another example, C ₁ -C ₆ alkoxy substituted with 1, 2 or 3 halogens is CH ₂ ClO-, CHCl ₂ O-, CCl ₃ O-, CH ₂ FO-, CHF ₂ O-, CF ₃ O -, may include a CF ₃ CH ₂ O- or CH ₃ CF ₂ O- group, but is not limited thereto.

As used herein, the term “hydroxyl” or “hydroxy” refers to the group —OH.

As used herein, the term "cyano" refers to the -CN group.

As used herein, the term “halogen” refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo).

As used herein, the term "C ₁ -C ₆ alkyl" refers to a straight chain or branched hydrocarbon chain radical consisting only of carbon and hydrogen atoms, containing no unsaturation, having 1 to 6 carbon atoms. , Which is attached to the rest of the molecule by a single bond. "C ₁ -C ₄ alkyl" and "C ₁ -C ₃ alkyl" should be interpreted accordingly. Examples of C ₁ -C ₆ alkyl include, but are not limited to, methyl, ethyl, n-propyl, and isomers thereof, such as iso-propyl.

As used herein, the term “C ₁ -C ₄ haloalkyl” refers to a C ₁ -C ₄ alkyl radical, as defined above, generally substituted by one or more of the same or different halogen atoms. Examples of C ₁ -C ₄ haloalkyl include, but are not limited to, trifluoromethyl.

As used herein, the term “hydroxyC ₁ -C ₄ alkyl” refers to a C ₁ -C ₄ alkyl radical, as defined above, generally substituted by one or more hydroxy groups.

As used herein, the term “cyanoC ₁ -C ₄ alkyl” refers to a C ₁ -C ₄ alkyl radical, as defined above, generally substituted by one or more cyano groups.

As used herein, the term “C ₂ -C ₆ alkenyl” contains at least one double bond that may have a ( E )- or ( Z )-configuration, having 2 to 6 carbon atoms. , A straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, which are attached to the rest of the molecule by a single bond. The term "C ₂ -C ₃ alkenyl" should be interpreted accordingly. Examples of C ₂ -C ₆ alkenyl include, but are not limited to, ethenyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), but-1-enyl.

As used herein, the term "C ₂ -C ₆ alkynyl" is a straight chain or branched hydrocarbon chain radical consisting only of carbon and hydrogen atoms, containing at least one triple bond, having 2 to 6 carbon atoms. Refers to a group, which is attached to the rest of the molecule by a single bond. The term "C ₂ -C ₃ alkynyl" should be interpreted accordingly. Examples of C ₂ -C ₆ alkynyl include, but are not limited to, ethynyl, prop-1-ynyl, butbut-1-ynyl.

As used herein, the term “C ₂ -C ₆ haloalkenyl” refers to a C ₂ -C ₆ alkenyl radical, as defined above, generally substituted by one or more of the same or different halogen atoms. do. Examples of C ₂ -C ₆ haloalkenyl include, but are not limited to, 2-fluorovinyl, 2,2-difluorovinyl, 2-chlorovinyl, and 2,2-dichlorovinyl.

As used herein, the term “C ₂ -C ₆ haloalkynyl” refers to a C ₂ -C ₆ alkynyl radical, as defined above, generally substituted by one or more of the same or different halogen atoms. do.

As used herein, the term “C ₁ -C ₄ alkoxy” refers to a radical of the formula —OR _a , where R _a is _a C ₁ -C ₄ alkyl radical, as generally defined above. "C ₁ -C ₃ alkoxy" should be interpreted accordingly. Examples of C ₁ -C ₄ alkoxy include, but are not limited to, methoxy, ethoxy, 1-methylethoxy (iso-propoxy), and propoxy.

As used herein, the term “C ₃ -C ₆ cycloalkyl” refers to a radical that is a monocyclic saturated ring system and contains 3 to 6 carbon atoms. The term "C ₃ -C ₄ cycloalkyl" should be interpreted accordingly. Examples of C ₃ -C ₆ cycloalkyl are cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclobutyl, 1-methylcyclobutyl, 1,1-dimethylcyclobutyl, 2-methylcyclobutyl, and 2 ,2-dimethylcyclobutyl.

As used herein, the term “heteroaryl” refers to a 5- or 6-membered aromatic monocyclic ring radical comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur. do. Examples of heteroaryl include furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidi Neil or pyridyl.

The presence of one or more possible asymmetric carbon atoms in the compound of formula (I) means that the compound can occur in the form of optical isomers, ie enantiomers or diastereomers. In addition, atropisomers can occur as a result of limited rotation around a single bond. Formula I is intended to include all such possible isomer forms and mixtures thereof. The present invention includes all such possible isomer forms for the compounds of formula I and mixtures thereof. Likewise, Formula I is intended to include all possible tautomers. The present invention includes all possible tautomeric forms for the compounds of formula (I).

In each case, the compounds of formula (I) according to the invention are present in free form, in oxidized form as N-oxide, or in salt form, for example agronomically useful salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. These are described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton (1991).

The following list provides definitions (including preferred definitions) for the substituents R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X with reference to compounds of Formula I. For any of these substituents, any definition provided below can be combined with any definition of any other substituent provided below or elsewhere herein.

R ¹ is halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ haloalkyl. Preferably, R ¹ is halogen, cyano, or C ₁ -C ₃ alkyl, more preferably chloro, fluoro, bromo, methyl, ethyl or isopropyl. Even more preferably, R ¹ is chloro or fluoro, and most preferably fluoro.

R ² is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl. Preferably, R ² is hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, or C ₃ -C ₄ cycloalkyl, more preferably hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, even more preferably hydrogen, methyl, ethyl, methoxy or ethoxy. Furthermore, more preferably, R ² is hydrogen or methoxy, and most preferably hydrogen.

R ³ is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl. Preferably, R ³ is halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkyl, or C ₃ -C ₄ cycloalkyl, more preferably halogen, C _1- C ₃ alkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkyl, even more preferably halogen or C ₁ -C ₃ alkyl. Further more preferably, R ³ is chloro, fluoro or methyl, even more preferably chloro or methyl, and most preferably R ³ is methyl.

R ⁴ is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl. Preferably, R ⁴ is hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, or C ₃ -C ₄ cycloalkyl, more preferably hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, even more preferably hydrogen, methyl, ethyl, methoxy or ethoxy. Furthermore, more preferably, R ⁴ is hydrogen or methoxy, and most preferably hydrogen.

R ⁵ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₆ haloalkenyl, C _2- C ₆ haloalkynyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moieties are nitrogen, oxygen and sulfur A 5 or 6 membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties, respectively, represented by R ⁷ Optionally substituted with 1 to 3 groups.

Preferably, R ⁵ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkynyl, C ₃ -C ₄ cycloalkyl, or phenyl, where C ₃ -C ₄ cycloalkyl and phenyl moiety Tees are each optionally substituted with 1 to 3 groups represented by R ⁷ . More preferably, R ⁵ is hydrogen, halogen, C ₁ -C ₃ alkyl, C ₂ -C ₃ alkynyl, or phenyl, wherein the phenyl moiety is optionally substituted with 1 or 2 groups represented by R ⁷ do. Even more preferably, R ⁵ is hydrogen, chloro, fluoro, bromo, methyl, ethyl, isopropyl, prop-2-ynyl, or phenyl, wherein the phenyl moiety is 1 or represented by R ⁷ It is optionally substituted with two groups. Further more preferably, R ⁵ is hydrogen, chloro, fluoro, methyl, ethyl, prop-2-ynyl, phenyl, 4-fluorophenyl or 4-chlorophenyl, and most preferably hydrogen or methyl .

R ⁶ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₆ haloalkenyl, C _2- C ₆ haloalkynyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moieties are nitrogen, oxygen and sulfur A 5 or 6 membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties, respectively, represented by R ⁷ Optionally substituted with 1 to 3 groups.

Preferably, R ⁶ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, or phenyl, wherein heteroaryl Moieties are 5- or 6-membered aromatic monocyclic rings containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur, and C ₃ -C ₆ cycloalkyl, phenyl, and heteroaryl moieties. Tees are each optionally substituted with 1 to 3 groups represented by R ⁷ . More preferably, R ⁶ is hydrogen, halogen, C ₁ -C ₃ alkyl, C ₂ -C ₃ alkenyl, C ₂ -C ₃ alkynyl, C ₃ -C ₄ cycloalkyl, phenyl or heteroaryl, wherein , Heteroaryl moieties are 5-membered aromatic monocyclic rings containing 1 or 2 heteroatoms individually selected from nitrogen, oxygen and sulfur, and C ₃ -C ₄ cycloalkyl, phenyl and heteroaryl moieties are each It is optionally substituted with 1 or 2 groups represented by R ⁷ . Even more preferably, R ⁶ is hydrogen, chloro, fluoro, bromo, methyl, ethyl, isopropyl, prop-2-enyl, prop-2-ynyl, cyclopropyl, cyclobutyl, phenyl, or thier Neil, wherein the phenyl and thienyl moieties are each optionally substituted with 1 or 2 groups represented by R ⁷ . Further more preferably, R ⁶ is hydrogen, chloro, fluoro, methyl, ethyl, prop-2-enyl, prop-2-ynyl, cyclopropyl, cyclobutyl, phenyl, 4-fluorophenyl, 2, 4-difluorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, or 3-methyl-2-thienyl, and most preferably, methyl, 2,4-difluorophenyl, 4-chlorophenyl , 2,4-dichlorophenyl, or 3-methyl-2-thienyl.

R ⁷ is halogen, cyano, hydroxyl, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, or C ₃ -C ₄ cycloalkyl. Preferably, R ⁷ is halogen, C ₁ -C ₃ alkyl, or C ₁ -C ₃ alkoxy, more preferably, chloro, fluoro, bromo, methyl, ethyl, isopropyl, methoxy, ethoxy or Isopropoxy, even more preferably, chloro, fluoro, bromo, methyl, or ethyl. Further more preferably, R ⁷ is chloro, fluoro or methyl.

In one embodiment, when R ⁵ is hydrogen or C ₁ -C ₃ alkyl, R ⁶ is C ₁ -C ₃ alkyl, phenyl, or thienyl, wherein the phenyl and thienyl moieties are each selected from R ⁷ Optionally substituted with 1 or 2 groups. Preferably, when R ⁵ is hydrogen or methyl, R ⁶ is C ₁ -C ₃ alkyl, phenyl, or thienyl, wherein the phenyl and thienyl moieties are each with 1 or 2 groups selected from R ⁷ Is optionally substituted. More preferably, when R ⁵ is hydrogen or methyl, R ⁶ is methyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl or 3-methyl-2-thienyl.

X is C-H or N. In one embodiment, X is C-H. In other embodiments, X is N.

In the compounds of formula I according to the invention, preferably,

R ¹ is halogen;

R ² and R ⁴ are each independently hydrogen or C ₁ -C ₃ alkoxy;

R ³ is halogen or C ₁ -C ₃ alkyl;

R ⁵ is hydrogen, halogen, C ₁ -C ₃ alkyl, C ₂ -C ₃ alkynyl, or phenyl, wherein the phenyl moiety is optionally substituted with 1 or 2 groups represented by R ⁷ ;

R ⁶ is hydrogen, halogen, C ₁ -C ₃ alkyl, C ₂ -C ₃ alkenyl, C ₂ -C ₃ alkynyl, phenyl, or heteroaryl, wherein the heteroaryl moiety contains 1 sulfur atom Is a 5-membered aromatic monocyclic ring, wherein the phenyl and heteroaryl moieties are each optionally substituted with 1 or 2 groups represented by R ⁷ ;

R ⁷ is chloro, fluoro, bromo, methyl, ethyl, isopropyl, methoxy, ethoxy or isopropoxy;

X is C-H or N.

More preferably, R ¹ is halogen;

R ² and R ⁴ are each independently hydrogen;

R ³ is C ₁ -C ₃ alkyl;

R ⁵ is hydrogen or C ₁ -C ₃ alkyl;

R ⁶ is C ₁ -C ₃ alkyl, phenyl, or heteroaryl, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1 sulfur atom, and the phenyl and heteroaryl moieties are each R ⁷ Is optionally substituted with 1 or 2 groups represented by;

R ⁷ is chloro, fluoro, or methyl;

X is N.

Even more preferably, R ¹ is fluoro;

R ² and R ⁴ are each independently hydrogen;

R ³ is methyl;

R ⁵ is hydrogen or methyl;

R ⁶ is methyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl or 3-methyl-2-thienyl;

X is N.

In one set of embodiments, R ¹ is halogen;

R ² and R ⁴ are each independently hydrogen;

R ³ is C ₁ -C ₃ alkyl;

R ⁵ is hydrogen or C ₁ -C ₃ alkyl;

R ⁶ is hydrogen, C ₁ -C ₃ alkyl, phenyl, or heteroaryl, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1 sulfur atom, and the phenyl and heteroaryl moieties are each Optionally substituted with 1 or 2 groups represented by R ⁷ ;

R ⁷ is chloro, fluoro, or methyl;

X is N.

In another set of embodiments, R ¹ is fluoro;

R ² and R ⁴ are each independently hydrogen;

R ³ is methyl;

R ⁵ is hydrogen or methyl;

R ⁶ is hydrogen, methyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl or 3-methyl-2-thienyl;

X is N.

Preferably, the compound according to formula I is

2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-(2-methylcyclobutyl)thiazole-4-carboxamide (Compound 1.c.19);

2-[(2,6-difluoro-4-pyridyl)amino]-N-(2-ethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Compound 1.d.19) ;

N-(2,2-difluorocyclobutyl)-2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxamide (Compound 1. p.19);

2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Compound 1.r. 19); And

N-(2,2-diethylcyclobutyl)-2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxamide (Compound 1.s .19).

The compounds of formula I according to the invention can have two chiral centers at carbon atoms A and B as outlined in formula A below.

[Formula A]

Accordingly, as already indicated, the compounds of formula (I) may exist in various diastereomeric forms, i.e. (S,S)-, (S,R)-, (R present on A and B carbons, respectively. ,R)-, or (R,S)-configuration. In particular, each of these batches is a table of each compound described in Table 1 (compounds of formulas (1.a.01-1.a.32) to (1.z.01-1.z.32)) or (below) For compounds of formula I described in ² it will be apparent for compounds of formula I in relation to certain combinations of definitions for R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , and X. will be.

The compounds of the present invention can be prepared as shown in the schemes below, where, unless stated otherwise, the definition of each variable is as defined above for the compound of formula (I).

The compounds of formula (I) according to the invention, wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and X are as defined for formula (I), by thermal heating, or Compounds of Formula II, wherein R ¹ , R ² and X are as defined for Formula I, with or without the conditions of transition metal catalyzed Buchwald-Hartwig amination Can be obtained by conversion with a compound of III, wherein R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for Formula I, and R ⁸ is bromo or iodo. This is shown in Scheme 1 below.

[Scheme 1]

Compounds of Formula III (where R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for Formula I, and R ⁸ is bromo or iodo) are compounds of Formula IV as peptide coupling agents (where , R ³ is as defined for Formula I, R ⁸ is bromo or iodo, and compounds of Formula V, wherein R ⁴ , R ⁵ and R ⁶ are as defined for Formula I It can be obtained by modifying. This is shown in Scheme 2 below.

[Scheme 2]

Alternatively, the compound of Formula III, wherein R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for Formula I, and R ⁸ is bromo or iodo. Wherein R ³ is as defined for Formula I, R ⁸ is bromo or iodo, R ⁹ is fluoro or chloro, and compounds of Formula V, wherein R ⁴ , R ⁵ and R ⁶ can be obtained by modifying (as defined for Formula I). This is shown in Scheme 3 below.

[Scheme 3]

A compound of Formula IV, wherein R ³ is as defined for Formula I, R ⁸ is bromo or iodo, and a compound of Formula VII as a base, wherein R ³ is as defined for Formula I Same, R ⁸ is bromo or iodo, and R ¹⁰ is C ₁ -C ₆ alkyl). This is shown in Scheme 4 below.

[Scheme 4]

Compounds of Formula VI, wherein R ³ is as defined for Formula I, R ⁸ is bromo or iodo, and R ⁹ is fluoro or chloro, is a halogenating agent of Formula IV, wherein R ³ is as defined for formula I, R ⁸ can be obtained by modifying bromo or iodo. This is shown in Scheme 5 below.

[Scheme 5]

Alternatively, a compound of Formula I, wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and X are as defined for Formula I, wherein the compound of Formula V, wherein R ⁴ , R ⁵ and R ⁶ are as defined for Formula I) and a peptide coupling agent to modify the compound of Formula VIII, wherein R ¹ , R ² , R ³ and X are as defined for Formula I Can be obtained. This is shown in Scheme 6 below.

[Scheme 6]

Alternatively, a compound of Formula I, wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and X are as defined for Formula I, wherein the compound of Formula V, wherein R ⁴ , R ⁵ and R ⁶ are as defined for Formula I and compounds of Formula IX as bases, wherein R ¹ , R ² , R ³ and X are as defined for Formula I, R ⁹ is Fluoro or chloro). This is shown in Scheme 7 below.

[Scheme 7]

Compounds of formula VIII (where R ¹ , R ² , R ³ and X are as defined for formula I) are compounds of formula X with base (where R ¹ , R ² , R ³ and X are formula I As defined for and R ¹⁰ is C ₁ -C ₆ alkyl). This is shown in Scheme 8 below.

[Scheme 8]

Compounds of formula IX, wherein R ¹ , R ² , R ³ and X are as defined for formula I, and R ⁹ is fluoro or chloro, are halogenated compounds of formula VIII, wherein R ¹ , R ² , R ³ and X can be obtained by modifying (as defined for formula I). This is shown in Scheme 9 below.

[Scheme 9]

The compounds of formula X according to the invention, wherein R ¹ , R ² , R ³ and X are as defined for formula I, R ¹⁰ is C ₁ -C ₆ alkyl, by thermal heating or by base With the aid of or under the conditions of a transition metal catalyzed Buchwald-Hartwig amination, a compound of Formula XI, wherein R ³ is as defined for Formula I, R ⁸ is bromo or iodo, R ¹⁰ is C ₁ -C ₆ alkyl) and can be obtained by modifying the compound of formula II, wherein R ¹ , R ² and X are as defined for formula I. This is shown in Scheme 10 below.

[Scheme 10]

Alternatively, a compound of Formula X, wherein R ¹ , R ² , R ³ and X are as defined for Formula I, and R ¹⁰ is C ₁ -C ₆ alkyl, is a transition metal catalyzed Buch. Compounds of Formula XII, wherein R ¹ and X are as defined for Formula I, and R ⁸ is bromo or iodo, under the conditions of Balt-Hartwig amination, wherein R ² and R ³ are as defined for Formula I, and R ¹⁰ can be obtained by conversion by C ₁ -C ₆ alkyl. This is shown in Scheme 11 below.

[Scheme 11]

Alternatively, the compounds of formula I according to the invention, wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and X are as defined for formula I, are transition metal catalyzed Compounds of formula XII (where R ¹ and X are as defined for formula I, R ⁸ is bromo or iodo) under the conditions of Buchwald-Hartwig amination, wherein , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ as defined for Formula I). This is shown in Scheme 12 below.

[Scheme 12]

Surprisingly, it has now been found that the novel compounds of formula (I) have, in fact, a very favorable level of biological activity in protecting plants against diseases caused by fungi.

The compounds of formula (I) can be used in the agricultural sector and related fields of use, for example, on inanimate materials or as active ingredients for controlling plant pests to control decaying microorganisms or organisms potentially harmful to humans. The new compounds are distinguished by their excellent activity at low application rates, by showing that plants exhibit good resistance and environmentally safety. They have very useful radical, prophylactic and systemic properties and can be used to protect many cultivated plants. Compounds of the formula (I) inhibit or control pests that occur on plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while also, for example, from phytopathogenic microorganisms , It can be used to protect parts of plants that grow later.

The present invention further relates to a method for controlling or preventing intrusion into plants or plant propagation materials and/or harvested edible crops susceptible to microbial attack by treating plants or plant propagation materials and/or harvested edible crops. As such, in this method, an effective amount of a compound of Formula I is applied to a plant, to a portion thereof, or to its habitat.

In addition, compounds of formula I can be used as fungicides. As used herein, the term "fungicide" means a compound that controls, modifies, or prevents the growth of fungi. The term “fungicidal effective amount” refers to the amount of such a compound or combinations of such compounds capable of producing an effect on the growth of the fungus. The control or modifying effect includes any deviation from natural development, such as death, delay, etc., and prevention includes the formation of barriers or other defenses in or on plants to prevent fungal infections.

In addition, in order to protect against fungal infections and against phytopathogenic fungi occurring in the soil, plant propagation materials, for example seeds, such as fruit, tubers or grains, or plant cutting (eg , Rice) it is possible to use compounds of formula I as dressing agents for the treatment. The propagation material can be treated with a composition comprising a compound of formula I before planting: for example, the seeds can be fractionated before sowing.

The active ingredient according to the invention can also be applied to the grain (coating) by immersing the seeds in a liquid formulation or by coating with a solid formulation. The composition can also be applied to a planting site when the propagation material is planted in the seed furrow, for example during sowing. The invention also relates to a method of treating a plant propagation material and a plant propagation material so treated.

Moreover, the compounds according to the invention can be used in the field to control fungi, for example in the protection of industrial materials, including wood and wood-related industrial products, in food storage and in hygiene management.

Moreover, the present invention can be used to protect inanimate materials from fungal attack, such as lumber, wall board and paint.

The compounds of formula I can be effective, for example, against fungal and fungal vectors of diseases, as well as phytopathogenic bacteria and viruses. These fungal and fungal vectors of the disease as well as phytopathogenic bacteria and viruses are, for example:

Absidia corymbifera , Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp., For example, A. flavus , A. fumigatus , A. nidulans , A. niger , A. terrus ), Aureobasidium species (Aureobasidium spp.), for example A. pullulans (A. pullulans), Blas Saturday, Mrs. Edith van der Matt Titi (Blastomyces dermatitidis), blue Grouse Almeria Mini bus (Blumeria graminis), Brenna Mia Rock tukayi (Bremia lactucae), boat Rio spy Ria species (Botryosphaeria spp.), for example, B. Dottie Oradea (B. dothidea), B. option projection (B. obtusa), Botrytis species (Botrytis spp.), for example B. B. cinerea , Candida spp., such as C. albicans , C. glabrata , C. krusei , C. C. lusitaniae , C. parapsilosis , C. tropicalis , Cephaloascus fragrans , Ceratocystis spp. ), Cercospora spp., such as C. arachidicola , Cercosporidium personatum , Cladosporium spp., Clavisporium spp. Claviceps purpurea , Coccidioides immitis , Cochliobolus spp., Colletotrichum spp., such as C. musae , Cryptococcus neoformman Cryptococcus neoformans , diaporthe spp., didymella spp., Drechslera spp., Elsinoe spp., Epidermophyton species ( Epidermophyton spp.), Erwinia amylovora , Erysiphe spp., such as E. cichoracearum , Eutypa lata , Fusarium species ( Fusarium spp.) such as F. culmorum , F. graminearum , F. langsethiae , F. moniliforme , F. oxysporum , F. proliferatum , F. subglutinan s, F. solani , F. solani Gaeumannomyces graminis , Gibberella fujikuroi , Gloeodes pomigena , Gloeosporium musarum , Glomerella cingulate , Guignardia bidwellii , Gymnosporangium juniperi-virginianae , Helminthosporium spp., Hemelia species ( Hem ileia spp.), histogram plasma species (Histoplasma spp.), for example, H. Cobb Peninsula Tomb (H. capsulatum), La ET Sarria Pookie formate miss (Laetisaria fuciformis), calligraphy repto help Lind suberic group (Leptographium lindbergi), Leveillula taurica , Lophodermium seditiosum , Microdochium nivale , Microsporum spp., Monilinia spp. , no kind of Cortez (Mucor spp.), Pasteurella species Mycobacterium Spy (Mycosphaerella spp.), for example, M. Gras Mini Coke (M. graminicola), M. breech (M. pomi), Teddy Stadium on kobasi of Rome ions (Oncobasidium theobromaeon , Ophiostoma piceae , Paracoccidioides spp., Penicillium spp., such as P. digitatum , P. italicum (P. italicum), Petri Ely Stadium species (Petriellidium spp.), Ross Perot, North Clematis species Fora (Peronosclerospora spp.), for example, P. Mai display (P. maydis), P. Philip pinene system (P. philippinensis) and P. sorghi , Peronospora spp., Phaeosphaeria nodorum , Phakopsora pachyrhizi , Phellinus igniarus , Fora species as PR (Phialophora spp.), poma species (Phoma spp.), PO heavily's Bt coke (Phomopsis viticola), blood Saratov Tora species (P hytophthora spp.), such as P. infestans , Plasmopara spp., such as P. halstedii , P. viticola , pleoses Pleospora spp., Podosphaera spp., such as P. leucotricha , Polymyxa graminis , Polymyxa betae, Pseudoser Pseudocercosporella herpotrichoides , Pseudomonas spp., Pseudoperonospora spp., such as P. cubensis , P. humuli ), pseudo away Jatra K. Pilar (Pseudopeziza tracheiphila), puksi California species (Puccinia spp.), for example, P. Day Hor (P. hordei), P. rekon dita (P. recondita), P. seuteuriyi FORT Miss (P striiformis ), P. triticina , Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp., such as P. duck P. oryzae , Pythium spp., such as P. ultimum , Ramularia spp., Rhizoctonia spp., Rizomucor fussil Rhizomucor pusillus , Rhizopus arrhizus , Rhynchosporium spp., Scedosporium spp., such as S. apiospe rmum ) and S. prolificans , Schizothyrium pomi ,

Klee's zloty California species (Sclerotinia spp.), Clematis Loti's help species (Sclerotium spp.), Species counts Astoria (Septoria spp.), For example, S. surf Room (S. nodorum), S. Tea Tree City (S. tritici ), Sphaerotheca macularis , Sphaerotheca fusca ( Sphaerotheca fuliginea ), Sporothorix spp., Stagonospora nodo Room (Stagonospora nodorum), the system required Leeum species (Stemphylium spp.), Stephen reum hirsutum (Stereum hirsutum), Tana tepo Ruth Cuckoo Marys (Thanatephorus cucumeris), Tea Ella pray system Bridge-cola (Thielaviopsis basicola), tilre Tia species ( Tilletia spp.), Trichoderma spp., such as T. harzianum , T. pseudokoningii , T. viride , Trico Trichophyton spp., Typhula spp., Uncinula necator , Urocystis spp., Ustilago spp., Venturia species ( Venturia spp.), such as V. inaequalis , Verticillium spp., and Xanthomonas spp.

Within the scope of the present invention, target crops and/or useful plants to be protected are typically perennial and annual crops, such as berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; Cereals, such as barley, corn (corn), millet, oats, rice, rye, sorghum, rymil and wheat; Fiber plants, such as cotton, flax, hemp, jute and sisal; Field crops, such as beet and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; Fruit trees, such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; Grasses, for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, st augustine grass ( St. Augustine grass) and Zoysia grass; Herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; Legumes such as beans, lentils, peas and soybeans; Nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios and walnuts; Palm, for example oil palm; Ornamental plants such as flowers, shrubs and trees; Other trees, such as cacao, coconut, olive and rubber trees; Vegetables, such as asparagus, eggplant, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, zucchini, rubaba, spinach and tomato; And vines, such as grapes.

The term “useful plant” is a herbicide or class of herbicides such as bromoxynil as a result of conventional methods of breeding or genetic engineering (eg HPPD inhibitors, ALS inhibitors such as prisulfuron, prosulfuron, and triplelock facilities) Useful for making resistance to furon, EPSPS (5-enol-pyroville-shkimate-3-phosphate-synthase) inhibitor, GS (glutamine synthetase) inhibitor) or PPO (protoporphyrinogen-oxidase) inhibitor It should be understood that it also includes plants. One example of a crop that has become resistant to imidazolinone, such as Imazamox, by conventional breeding methods (mutation) is Clearfield® summer rapeseed (canola). Examples of crops that have been made tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant corn varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

The term “useful plant” is so transformed using recombinant DNA techniques capable of synthesizing one or more selectively functional toxins, for example those known to be derived from toxin-producing bacteria, particularly those from the genus Bacillus. It should be understood to also include useful plants that have been converted.

Examples of such plants are: YieldGard® (a corn variety expressing the CryIA(b) toxin); YieldGard Rootworm® (a corn variety expressing the CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing CryIA(b) and CryIIIB(b1) toxins); Starlink® (maize variety expressing Cry9(c) toxin); Herculex I® (a corn variety expressing the phosphinothricin N-acetyltransferase (PAT) enzyme and CryIF(a2) toxin to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton strain expressing CryIA(c) toxin); Bollgard I® (cotton variety expressing CryIA(c) toxin); Bollgard II® (cotton strain expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (cotton strain expressing VIP toxin); NewLeaf® (a potato strain expressing the CryIIIA toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-resistant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn root trait) and Protecta®.

The term “crop” is so transformed using recombinant DNA techniques capable of synthesizing one or more selectively functional toxins, for example those known to be derived from toxin-producing bacteria, in particular those from the genus Bacillus. It should be understood that the crop plants also include.

Toxins that can be expressed by such transgenic plants include, for example, live insect from Bacillus cereus (Bacillus cereus) or Bacillus Four pilriahyi (Bacillus popilliae) protein; Or an insecticidal protein from Bacillus thuringiensis , such as a δ-endotoxin, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or an insecticidal protein associated with plant growth (vegetative insecticidal protein, Vip), for example Vip1, Vip2, Vip3 or Vip3A; Or bacterial colony nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens , Xenorhabdus nematophilus ) Insecticidal protein; Toxins produced by animals such as scorpion toxin, spider toxin, wasp toxin and other insect-specific neurotoxins; Toxins produced by fungi, such as Streptomyces micro-test (Streptomycetes) toxin; Plant lectins, such as pea lectin, barley lectin or snowdrop lectin; Aglutinin; Proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; Ribosome-inactivating proteins (RIP), such as lysine, maize-RIP, abrin, lupine, saporin or bryodine; Steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium channel blockers, Larval hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

In the context of the present invention, a δ-endotoxin such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or an insecticidal protein associated with plant growth (Vip), such as Vip1, Vip2, Vip3 Or it should be understood that Vip3A is also expressed as a hybrid toxin, truncated toxin and modified toxin. Hybrid toxins are produced recombinantly by new combinations of different domains of these proteins (see eg WO 02/15701). Cleavage toxins, such as Cry1Ab cleavage, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. Upon such amino acid replacement, a native non-existent protease recognition sequence is preferably inserted into the toxin, for example, in the case of Cry3A055, the cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesizing such toxins are, for example, EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529 , EP-A-451 878 and WO 03/052073.

Methods of making such transgenic plants are generally known to those skilled in the art and are described, for example, in the aforementioned publications. CryI type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

Toxins contained in transgenic plants confer resistance to harmful insects to plants. These insects can occur in any insect classification group, but are particularly commonly found in the coleoptera (Coleoptera), the dicetic insect (Paspidoptera) and the butterfly (Panthera).

Transgenic plants containing one or more genes that code for insecticidal resistance and express one or more toxins are known, some of which are commercially available. Examples of such plants are: YieldGard® (a corn variety expressing the Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin); YieldGard Plus® (corn variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing Cry9C toxin); Herculex I® (corn variety expressing the phosphinothricin N-acetyltransferase (PAT) enzyme and Cry1Fa2 toxin to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variant expressing Cry1Ac toxin); Bollgard I® (cotton variant expressing Cry1Ac toxin); Bollgard II® (cotton strain expressing Cry1Ac and Cry2Ab toxins); VipCot® (cotton strain expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato strain expressing the Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-resistant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Additional examples of such transgenic crops are:

1.Bt11 corn (manufacturer: Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10). Transgenic Cry1Ab toxin, transgenic Zea mays that have been resistant to attacks by European corn borers ( Ostrinia nubilalis and Sesamia nonagrioides ) mays ). Bt11 corn also expresses the enzyme PAT by transduction to achieve resistance to the herbicide glufosinate ammonium.

2. Bt176 corn (manufacturer: Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10). Genetically modified Zea mays that has been made resistant to attacks by European corn borers (Austriania nubilalis and Sesameia nonagrioides) by transgenic expression of the Cry1Ab toxin. Bt176 corn also expresses the enzyme PAT by transduction to achieve resistance to the herbicide glufosinate ammonium.

3. MIR604 corn (manufacturer: Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10). Corn made insect-resistant by transgenic expression of the modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03/018810.

4.MON 863 corn (manufacturer: Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9). MON 863 expresses the Cry3Bb1 toxin, and is resistant to certain Coleoptera insects.

5. IPC 531 cotton (manufacturer: Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number: C/ES/96/02).

6. 1507 corn (manufacturer: Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10). Genetically modified corn for the expression of the protein Cry1F to achieve resistance to certain lepidopteran insects and the PAT protein to achieve resistance to the herbicide glufosinate ammonium.

7.NK603 x MON 810 corn (manufacturer: Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03). It consists of hybrid corn varieties that are typically bred by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 corn is protein CP4 EPSPS obtained from Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (containing glyphosate), and also prescribed including European corn borer The Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki , which causes resistance to the human tree, is expressed by transduction.

As used herein, the term "habitat" means a field in which the plant is growing in or above, or where the seed of a cultivated plant is sown, or where the seed will be placed in the soil. It includes established vegetation as well as soil, seeds, and seedlings.

The term "plant" refers to all body parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.

The term "plant propagation material" is understood to denote a plant's germative parts, such as seeds, and vegetative materials, such as shovels or tubers, such as potatoes, which can be used for plant propagation. For example, seeds (in a strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants can be mentioned. Germinated plants and young plants that must be transplanted after germination from the soil or after germination may also be mentioned. These young plants can be protected prior to transplantation by total or partial treatment by immersion. It is understood that preferably "plant propagation material" refers to the seed.

Insecticides referred to herein using the common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.

The compounds of formula (I) can be used in unmodified form or, preferably, with adjuvants commonly used in the field of formulations. For this purpose, they are emulsifiable concentrates, coatable pastes, direct sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders in a known manner. (soluble powder), dust, granulate, and also can be formulated for convenience in the form of encapsulation into, for example, polymeric materials. As with the type of composition, the method of application, such as spraying, atomizing, dusting, scattering, coating or injection, is selected according to the intended purpose and prevailing circumstances. The composition may also contain additional adjuvants, such as stabilizers, anti-foaming agents, viscosity modifiers, binders or tackifiers, as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

For example, carriers and adjuvants suitable for agricultural use can be solid or liquid, and are useful for formulation techniques, for example natural or renewable mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers to be. Such carriers are described, for example, in WO 97/33890.

The compound of formula (I) is usually used in the form of a composition and can be applied to the plant or crop area to be treated, simultaneously or continuously with additional compounds. Such additional compounds can be, for example, fertilizers or micronutrient feedstocks, or other preparations that affect plant growth. They may also be selective herbicides or non-selective herbicides, as well as insecticides, fungicides, fungicides, nematodes, molluscs or mixtures of several of these preparations, if necessary Additional carriers, surfactants or application promoting adjuvants customarily used in the field may be present together.

The compound of formula (I) is, as active ingredient, at least one compound of formula (I) in free form or in the form of an agrochemically useful salt, or at least one preferred individual compound as defined above, and at least one above-mentioned adjuvant It can be used in the form of a (fungicidal) composition for controlling or protecting against phytopathogenic microorganisms, including burnt.

The present invention provides a composition comprising at least one compound of formula I, an agriculturally acceptable carrier and optionally an adjuvant, preferably a fungicidal composition. Agriculturally acceptable carriers are, for example, carriers suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may comprise, in addition to the compound of the formula (I), at least one or more pesticidal active compounds, for example additional fungicidal active ingredients.

The compound of formula (I) may be the only active ingredient of the composition, or it may be admixed, if appropriate, with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides or plant growth regulators. In some cases, additional active ingredients can lead to unexpected synergistic activity.

Examples of suitable additional active ingredients include the following acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone killers Fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, vegetable fungicides, cross-linked diphenyl fungicides, carbamate fungicides, carbanate fungicides, conazole fungicides , Copper fungicide, dicarboximide fungicide, dinitrophenol fungicide, dithiocarbamate fungicide, dithiolane fungicide, furamide fungicide, furanilide fungicide, hydrazide fungicide, imidazole Fungicides, mercury fungicides, morpholine fungicides, organophosphorus fungicides, organotin fungicides, oxathiine fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine Fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazoles Fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides Fungicides are included.

Examples of suitable additional active ingredients also include:

3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl )-Amide, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]- Amide, 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71- 1), 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl)-amide, 1-methyl-3-difluoro Lomethyl-4H-pyrazole-4-carboxylic acid [2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide, (5-chloro-2,4-dimethyl -Pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, (5-bromo-4-chloro-2-methoxy-pyridin-3-yl) -(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, 2-{2-[(E)-3-(2,6-dichloro-phenyl)-1-methyl-prop -2-ene-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide, 3-[5-(4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl]-pyridine, (E)-N-methyl-2-[2-(2, 5-dimethylphenoxymethyl) phenyl]-2-methoxy- Iminoacetamide, 4-bromo-2-cyano-N, N-dimethyl-6-trifluoromethylbenzimidazole-1-sulfonamide, a-[N-(3-chloro-2, 6- Xylyl)-2-methoxyacetamido]-y-butyrolactone, 4-chloro-2-cyano-N, -dimethyl-5-p-tolylimidazole-1-sulfonamide, N-allyl -4, 5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide, N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) propionamide , N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, (.+-.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4- Triazole-1-yl)-cycloheptanol, 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propane- 2-ol, 2',6'-dibromo-2-methyl -4-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole- 5-carboxanilide, 1-imidazolyl-1-(4'-chlorophenoxy)-3,3- Dimethylbutan-2-one, methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate, methyl (E)- 2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[6-(2 -Fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidine -4-yloxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate , Methyl (E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2- [3-(phenyl-sulfonyloxy)phenoxy]phenyl-3-methoxyacrylate, methyl (E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3- Methoxyacrylate, methyl (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3,5-dimethyl-benzoyl)pyrrole-1- 1]-3-methoxyacrylate, methyl (E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl (E)-2[2-(2- Phenylethen-1-yl)-phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylic Late, methyl (E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate, methyl (E)-2- (2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate, methyl (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl) -3-methoxyacrylate, methyl (E)-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methoxyacrylate, methyl (E)-2-[2-(3 -Isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate , Methyl (E)-2-[2-(3-ethoxyphenoxy C)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl (E) -2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[(3-methyl-pyridine-2- Iloxymethyl)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxy Acrylate, methyl (E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3- (3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyridine Midin-4-yloxy]phenyl]-3-methoxyacrylate, methyl (E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloxyminomethyl)phenyl]- 3-methoxyacrylate, methyl (E)-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-acrylate, Methyl (E),(E)-2-{ 2-(3-methoxyphenyl)methyloxyminomethyl]-phenyl}-3-methoxyacrylate, methyl (E)-2-{2-(6- (2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, methyl (E),(E)-2-{2-[6-phenylpyrimidin-4- 1)-methyloxyminomethyl]phenyl}-3-methoxyacrylate, methyl (E),(E)-2-{2-[(4-chlorophenyl)-methyloxyminomethyl]-phenyl}-3 -Methoxyacrylate, methyl (E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxy Acrylate, methyl (E), (E)-2-{2-[(3-nitrophenyl)methyloxyminomethyl]phenyl}-3-methoxyacrylate, 3-chloro-7-(2-aza- 2,7,7-trimethyl-oct-3-ene-5-yn), 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propynyl alcohol , 4-chlorophenyl-3-iodopropargyl formal, 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diyo Do-2-propenyl alcohol, 3-iodo-2-propynyl n-butylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate, 3-iodo-2-propynyl cyclo Hexyl-carbamate, 3-iodo-2-propynyl phenylcarbamate; Phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, 5-hydroxy-2(5H)-furanone; 4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone, 4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3- On, 3,5-dimethyl-tetrahydro-1,3,5-thiadiazine-2-thione, N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acifetax, al Ranicarb, albendazole, aldimorph, allicin, allyl alcohol, amethoxtradine, amisulbrom, amobam, ampropylphos, anilazine, asomate, aureofungin, azaconazole, azafendine, Azitiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanyl, benomyl, benquinox, bentaluron, benthiavaliccarb, benthiazole, benzalkonium chloride, benzamacryl, benza Morph, benzohydroxamic acid, benzovindiflupyr, berberine, betoxazine, biloxazole, binapacryl, biphenyl, bitteranol, bithionol, bixafen, blasticidin-S, boscalid, bromotal Ronil, bromuconazole, burimate, butiobate, butylamine calcium polysulfide, captapol, captan, carbamorph, carbendazim, carbendazim chlorhydrate, carboxyl, carpropamide, carb Carvone, CGA41396, CGA41397, chinomethionate, chitosan, clobenthiazone, chloraniformmethane, chloranil, chlorphenazole, chloronep, chloropicrin, chlorotalonyl, chlorozolinate, clozolinate, Klimbazole, clotrimazole, clozilacon, copper-containing compounds such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, Copper sulphate, copper phthalate, copper zinc chromate and Bordeaux mixture, cresol, cupraneb, cuprobam, cuprous oxide, cyazofamide, cyclofuramide, cycloheximide, cyflufenamide, Simoxanil, cifendazole, ciproconazole, ciprodinil, dazomet, devacarb, decapentin, dehydroacetic acid, di-2-pyridyl disulfide 1,1'-dioxide, diclofluanid, diclo Mezin , Diclones, dichlorans, dichlorophenes, diclozolines, diclobutrazols, diclosimemet, dietetofencarb, diphenoconazole, diphenzoquat, diflumetorim, O-di-iso-propyl -S-benzyl thiophosphate, dimefluazole, dimethaclon, dimethconazole, dimethomorph, dimethirimol, diconazole, diconazole-M, dinobutone, dinocap, dinoctone, dino Fenton, dinosulfone, dinoterbone, diphenylamine, dipyrithione, disulfiram, dithalimphos, dithianon, dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodisine, dodine, doguadine, Drazosolone, edifenphos, enestrobolin, epoxyconazole, etaconazole, ethem, etaboxam, etirimol, ethoxyquin, ethyllysine, ethyl (Z)-N-benzyl-N([methyl(methyl -Thioethylideneamino-oxycarbonyl)amino]thio)-β-alaninate, etridiazole, pamoxamone, phenamidone, phenaminosulf, fenafanyl, fenarimol, fenbuconazole, fenfuram , Fenhexamide, phenitropan, phenoxanil, fenpiclonil, fenpicoxamide, fenpropidine, fenpropimorph, fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, perimzone, Fluazinam, fludioxonil, flumetober, flumorph, flupicolide, fluopyram, fluoroimide, fluorotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, Flutanil, Plutolanil, Flutriapol, Fluxapyroxad, Folpet, Formaldehyde, Fosetyl, Puberidazole, Furalaxyl, Furammetir, Purcarbanil, Furconazole, Purfural, Purmecyclox , Furofanate, gliodine, griseofulvin, guazatine, halacrenate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiophos, hydradrafen, hydroxyisoxazole, Hymexazole, imazalyl, imazalyl sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, inezine, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, ipro Balicarb, isopropanyl butyl carbamate, isoprothiolane, isopyrazam, isotianil, isovaledione, zofamphos, cara Sugamycin, creoxime-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamide, maneb, mebenyl, mecarbinzide, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, 2nd chloride Mercury, mercury chloride, pentyldinocap, metalaxyl, metalaxyl-M, metham, metazosolone, metconazole, metasulfocarb, metfuroxam, methyl bromide, methyl iodide, methyl isothiosia Nate, Methiram, Methiram-Zinc, Metominostrobin, Metraphenone, Metsulfobox, Milneb, Moroxidine, Michaellobutanyl, Michaelozoline, Nabam, Natamycin, Neoazogene, Nickel Dimethyldithiity Ocarbamate, nitrostyrene, nitro-iso-propyl, noarimol, octylinone, ofoprace, organo-mercury compounds, orisastrobin, ostol, oxadixyl, oxasulfuron, oxathiapyroline, auxin- Copper, oxolinic acid, oxconazole, oxycarboxine, farinol, pefurazoate, fenconazole, phenicuron, fenflufen, pentachlorophenol, fenthiopyrad, phenacrylacryl, phenazine oxide, phosdifen , Fosetyl-Al, phosphoric acid, phthalide, picoxystrobin, piperline, polycarbamate, polyoxin D, polyoxrim, polyram, probenazole, prochloraz, procimidone, propamidine, Propamocarb, propiconazole, propineb, propionic acid, proquinazide, prothiocarb, prothioconazole, pidiflumetofen, pyracarbolide, pyraclostrobin, pyrametrozrobin, pyraoxy Strobine, pyrazophos, pyribencarb, pyridinitrile, pyriphenox, pyrimethanil, pyriophenone, pyroquilon, pyroxcyclo, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinacetol , Quinazamide, quinconazole, quinomethionate, quinoxyfen, quintogen, rabenzazol, santonin, cedaxane, silthiofam, cimeconazole, sipconazole, sodium pentachlorophenate, spiroxamine , Streptomycin, Sulfur, Sultrofen, Tebuconazole, Teffloquine, Teclophthalam, Technagen, Tecoram, Tetraconazole, Thiavendazole, Thiadifluor, Thiophene, Thifluzamide, 2- (Thiocyanomethylthio)benzothiazole, thiophanate-methyl, thioqui Knox, thiram, thiadinil, thymibenconazole, thioxymid, tolclophos-methyl, tolyl fluanid, triadimephone, triadimenol, triamiphos, triarimol, triazbutyl, triazide , Tricyclazole, tridemorph, trioxystrobin, triflumazole, triporine, triflumisol, triticonazole, uniconazole, urvaside, validamycin, baliphenate, bafam, vinclozoline , Zarylamide, zineb, ziram and joxamide.

The compounds of the present invention can also be used in combination with an anthelmintic agent. Such anthelmintics are ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, celamectin, moxidectin, nemaddectin as described in EP-357460, EP-444964 and EP-594291. And compounds selected from the macrocyclic lactone class of compounds such as milbemycin derivatives. Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxpendazole, oxybendazole, parbendazole, and other members of this class. . Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisol, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include flukisides such as triclabendazole and chlorsulone and sestosides such as praziquantel and epsifrantel.

The compounds of the invention are not only derivatives and analogs of the paraherquamid/markportin family of anthelmintic agents, but also antiparasitic oxazolines such as those disclosed in US-5478855, US-4639771 and DE-19520936 It can be used in combination.

The compounds of the present invention are derivatives and analogs of the general class of dioxomorpholine parasites as described in WO-9615121, and also anthelmintic cyclic depsipeptides such as WO-9611945, WO-9319053, WO -9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538.

The compounds of the present invention may include other ectoparasiticides such as fipronil; Pyrethroid; Organophosphate; Insect growth regulators, such as lufenuron; Ecdysone agonists such as tebufenozide, etc.; Neonicotinoids, such as imidacloprid, and the like can be used.

The compounds of the present invention can be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Nos. WO 95/19363 or WO 04/72086, especially the compounds disclosed therein.

Other examples of such biologically active compounds that can be used in combination with the compounds of the present invention include, but are not limited to:

Organophosphates: Acetate, Azametiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, Kadusaphos, Chlorethoxyphos, Chlorpyriphos, Chlorfenbinphos, Chlormephos , Demethone, Demethone-S-methyl, Demethone-S-methyl sulfone, diallyphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfotone, ethion, ethopropos, ethrim Phosphor, pampur, phenamiphos, phenythion, pensulfothion, pention, flupyrazophos, phonophos, formomothion, phosphatizate, heptenophos, isazophos, isothioate, isox Sathion, Malathion, Metacriphos, Metamidosphos, Methidathione, Methyl-parathione, Mevinphos, Monocrotophos, Naled, Ometoate, Oxidemethone-methyl, Paraoxone, Parathion, Parathion-methyl , Pentoate, fosalone, phospholan, phosphocarb, fosmetone, phosphatidone, forrate, oxime, pyrimiphos, pyrimiphos-methyl, propenophos, propaphos, protamphos, Prothiophos, pyraclophos, pyridafenthion, quinalphos, sulfophos, temephos, terbuphos, tebupyrimphos, tetrachlorvinphos, thimetone, triazophos, trichlorphone, bamido Thion.

Carbamate: alaniccarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfane, cloetocarb, ethiophene carb, Phenoxycarb, penthiocarb, furiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, metomil, 5-methyl-m-cumenylbutyryl (methyl) Carbamate, oxamyl, pyrimicarb, propoxur, thiodicarb, thiopanox, triamate, UC-51717.

Pyrethroids: acritine, aletrin, alphamethrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolane-3-ylidene Methyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioalethrin, bioalethrin ((S)-cyclopentyl isomer), biore Smetrin, Bifenthrin, NCI-85193, Cycloprotrin, Cyhalothrin, Sititrin, Cyfenothrin, Deltamethrin, Emfenthrin, Espenvalerate, Etopenrox, Penfluthrin, Fenpropartrin, fenvalerate, flucilinate, flumethrin, fluvalinate (D isomer), imiprotrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prale Trine, pyrethrin (natural product), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluorene, t-fluvalinate, tefluthrin, tralomethrin, zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylurea: chlorfluazuron, difluvenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflu Benzuron, triflumuron, bupropezin, diophenollan, hexythiazox, ethoxazole, chlorpentaazine; b) ecdysone antagonists: halopenozide, methoxyphenozide, tebufenozide; c) Juvenoids: pyriproxyfen, methoprene (including S-methoprene), phenoxycarb; d) Lipid biosynthesis inhibitors: spirodiclofen.

Other antiparasitic agents: acequinosyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultop, bifenazite, vinapacryl, bromopropylate, BTG- 504, BTG-505, camphorchlor, cartap, chlorobenzylate, chlordimeform, chlorfenapyr, chromafenozide, clotianidin, cyromazine, diacloden, diafenthiuron, DBI-3204, D Nactin, Dihydroxymethyldihydroxypyrrolidine, Dinobutone, Dinocap, Endosulfane, Etiprole, Etofenprox, Phenazaquin, Flumite, MTI-800, Penpyroximate, Fluacrypyrim, Flubenzimin , Flubrositelinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydramethylnon, IKI-220, carnemite, NC-196, neem guard, nidinorterfuran , Nitenpyram, SD-35651, WL-108477, pyridaryl, propargite, protrifenbut, pymetrozine, pyridaben, pyrimidifen, NC-1111, R-195, RH-0345, RH-2485 , RYI-210, S-1283, S-1833, SI-8601, cilafluorene, cilomadin, spinosad, tebufenpyrad, tetradiphone, tetranactin, thiacloprid, thiocyclam, thiametoxam, Tolfenpyrad, triazamate, triethoxysphinosine, trinactin, berbutin, betalek, YI-5301.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

Fungicides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enfloxacin, fenbantel, phenetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, thiamuline, benazapril, pyriprole, cefquinom, florfenicol , Buserelin, cetobeccin, tulathromycin, ceftyur, carpropene, metaflumizone, praziquarantel, triclabendazole.

Another aspect of the invention is an insect or phytopathogenic microorganism in a plant, for example a useful plant, such as a crop plant, its propagation material, such as seeds, harvested crops, such as harvested edible crops, or inanimate materials, Preferably comprises a compound of formula (I) or a preferred individual compound as defined above, at least one compound of formula (I) or at least one preferred individual compound as defined above, for controlling or preventing invasion of fungal organisms. Use of a fungicidal or insecticidal mixture comprising a composition, or at least one compound of formula I or at least one preferred individual compound as defined above, in admixture with other fungicides or insecticides as described above It is about.

A further aspect of the invention provides an insect to a plant, for example a useful plant, such as a crop plant, its propagation material, such as seeds, harvested crops, such as harvested edible crops, or inanimate materials, or humans. A method for controlling or preventing the invasion of potentially harmful phytopathogenic or decaying microorganisms or organisms, in particular fungal organisms, wherein the method comprises, as an active ingredient, a compound of formula I or a preferred individual compound as defined above, Application to parts of a plant or its habitat, to its propagation material, or to any part of an inanimate material.

Control or prevention means reducing the penetration of insects, or potentially harmful phytopathogenic or decaying microorganisms or organisms, especially fungal organisms, to a level where improvement is demonstrated.

A preferred method of controlling or preventing the invasion of phytopathogenic microorganisms, particularly fungal organisms, or insects, into crop plants, comprising the application of a compound of formula (I), or an agrochemical composition containing at least one of the above compounds, is foliar application . The frequency of application and rate of application will depend on the corresponding pathogen or insect infestation risk. However, the compound of formula (I) can also be planted through the soil through the roots, by drenching the habitat of the plant in a liquid formulation, or by applying the compound to the soil in solid form, for example in the form of granules (soil application). Can penetrate (invasive action). In water rice crops, these granules can be applied to fresh water paddy fields. The compounds of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of fungicides or coating them with a solid formulation.

Compositions containing, for example, a solid or liquid adjuvant or monomer for encapsulating a compound of formula (I), and, if necessary, a compound of formula (I), in a known manner, typically, the compound is a bulking agent, such as a solvent, It can be prepared by intimate mixing and/or grinding with a solid carrier, and optionally a surface active compound (surfactant).

An advantageous application rate is usually 5 g to 2 kg of active ingredient (a.i.)/hectare (ha), preferably 10 g to 1 kg a.i./ha, most preferably 20 g to 600 g a.i./ha. When used as a seed drenching agent, a convenient dosage is 10 mg to 1 g of active substance per kg of seed.

When the combination of the present invention is used to treat seeds, the application rate of 0.001 to 50 g of compound of formula I per kg of seed, preferably 0.01 to 10 g of compound of formula I per kg of seed, is generally sufficient. .

The following mixtures of compounds of formula I and active ingredients are preferred. The abbreviation “TX” is one selected from the group of compounds 1.a.01-1.a.32 to 1.z.01-1.z.32 described in Table 1, and compounds described in Table 2 (below). Means a compound of:

Petroleum oil (alternative name) 628 + adjuvant selected from the group of substances consisting of TX,

1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC/chemical abstract name) (1059) + TX, 2 -Fluoro- N -methyl- N -1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX, abamectin (1) + TX, Acequinosyl (3) + TX, acetoprole [CCN] + TX, acrinatrine (9) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, alpha-cypermethrin ( 202) + TX, amidionion (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amitone (875) + TX, amitone hydrogen oxalate (875) + TX, Amitraz (24) + TX, Aramid (881) + TX, Arsenic Oxide (882) + TX, AVI 382 (Compound Code) + TX, AZ 60541 (Compound Code) + TX, Azinphos-ethyl (44) + TX, Azinphos-methyl (45) + TX, Azobenzene (IUPAC name) (888) + TX, Azocyclotin (46) + TX, Azotoate (889) + TX, Benomyl (62) + TX, Benoxaphos (Alternative Name) [CCN] + TX, Benzoxymate (71) + TX, Benzyl Benzoate (IUPAC name) [CCN] + TX, Biphenazite (74) + TX, Bifenthrin (76) + TX, Vinapacryl (907) + TX, Brofenvalerate (alternative name) + TX, Bromocyclen (918) + TX, Bromophos (920) + TX, Bromophos-ethyl ( 921) + TX, bromopropylate (94) + TX, bupropezin (99) + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphorchlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, Carbophenotion (947) + TX, CGA 50'43 9 (Development Code) (125) + TX, Kinomethionat (126) + TX, Chlorbenside (959) + TX, Chlordimeform (964) + TX, Chlordimeform hydrochloride (964) + TX, Chlorfenapyr (130) + TX, Chlorphenitol (968) + TX, Chlorphenson (970) + TX, Chlorfensulphide (971) + TX, Chlorphenbinphos (131) + TX, Chlorobenzylate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX, chloropropylate (983) + TX, chlorpyriphos (145) + TX, chlorpyriphos-methyl (146) + TX, Chlorthiophos (994) + TX, Cinerine I (696) + TX, Cinerine II (696) + TX, Cinerine (696) + TX, Clofenthezin (158) + TX, Closantel (alternative name) [CCN] + TX, Couma Force (174) + TX, Chromamiton (Alternative Name) [CCN] + TX, Crothoxyphos (1010) + TX, Cupraneb (1013) + TX, Cyanate ( 1020) + TX, Cyflumetofen (CAS registration number: 400882-07-7) + TX, Cyhalothrin (196) + TX, Cyhexatin (199) + TX, Cypermethrin (201) + TX, DCPM(1032) + TX, DDT(219) + TX, Demethion(1037) + TX, Demethion-O(1037) + TX, Demethion-S(1037) + TX, Demeton(1038) + TX, Demetone-methyl (224) + TX, Demetone-O (1038) + TX, Demetone-O-methyl (224) + TX, Demetone-S (1038) + TX, Demetone-S- Methyl (224) + TX, Demethone-S-methylsulfone (1039) + TX, Diafenthiuron (226) + TX, Dialiphos (1042) + TX, Diazinon (227) + TX, Diclofluani DE(230) + TX, Dichlorvos(236) + TX, Diclifos(Alternative Name) + TX, Dicopol(242) + TX, Dicrotopos(243) + TX, Dienochlor(1071) + TX, Dimepox (1081) + TX, Dimethoate (262) + TX, Dinactin (Alternate Name) (653) + TX, Dinex (1089) + TX, Dinex-Declexin (1089) + TX, Dinobutone (269) + TX , Dinocap(270) + TX, Dinocap-4[CCN] + TX, Dinocap-6[CCN] + TX, Dinoctone(1090) + TX, Dinophentone(1092) + TX, Dinosulfone(1097) + TX, dinoterbone (1098) + TX, dioxathion (1102) + TX, diphenyl sulfone (IUPAC name) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfotone ( 278) + TX, DNOC (282) + TX, dofenapine (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothion (1121) + TX, EPN ( 297) + TX, Eprinomectin (Alternative Name) [CCN] + TX, Ethion (309) + TX, Ethoate-methyl (1134) + TX, Etoxazole (320) + TX, Ethrimphos (1142) + TX, phenazaflor (1147) + TX, phenazaquin (328) + TX, fenbutatin oxide (330) + TX, phenothiocarb (337) + TX, fenpropartrine (342) + TX, Penpyrad (Alternative Name) + TX, Penpyroximate (345) + TX, Penson (1157) + TX, Pentrifanil (1161) + TX, Penvalerate (349) + TX, Fipronil (354) + TX, fluacrypyrim (360) + TX, fluazuron (1166) + TX, flubenzimin (1167) + TX, flucycloxuron (366) + TX, flucylinate (367) + TX, Fluenetyl (1169) + TX, Flufenoxuron (370) + TX, Flumetrin (372) + TX, Fluorbenside (1174) + TX, Fluvalinate (1184) + TX, FMC 1137 (Development Code) (1185) + TX, Formatenate (405) + TX, Formatenate hydrochloride (405) + TX, Formion (1192) + TX, Formparanate (1193) + TX, Gamma-HCH ( 4 30) + TX, Glyodine (1205) + TX, Halfenprox (424) + TX, Heptenophos (432) + TX, Hexadecyl cyclopropanecarboxylate (IUPAC/chemical abstract) (1216) + TX, Hexythiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, isopropyl O- (methoxyaminothiophosphoryl) salicy Silate (IUPAC name) (473) + TX, Ivermectin (alternative name) [CCN] + TX, Jasmoline I (696) + TX, Jasmoline II (696) + TX, Zodfenphos (1248) + TX, Lindan (430) + TX, Lufenuron (490) + TX, Malathion (492) + TX, Malonoven (1254) + TX, Mecarbam (502) + TX, Mephospolan (1261) + TX, Mesulfene (Alternative Name) [CCN] + TX, Metacripos (1266) + TX, Metamidosphos (527) + TX, Methidathion (529) + TX, Methiocarb (530) + TX, Me Temil (531) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinphos (556) + TX, mexarcarbate (1290) + TX, Milbemectin (557) + TX, Milbe Mycin Oxime (Alternative Name) [CCN] + TX, Mifapox (1293) + TX, Monocrotoforce (561) + TX, Morphothion (1300) + TX, Moxidectin (Alternative Name) [CCN] + TX, Nalred (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluridide (1309) + TX, nickomycin (alternative name) [CCN] + TX , Nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, ometoate (594) + TX, Oxamyl (602) + TX, Oxidepropos (1324) + TX, Oxydisulfonone (1325) + TX, pp'-DDT (219) + TX, Parathion (615) + TX , Permethrin (626) + TX, Petroleum Oil (Alternative Name) (628) + TX, Pencapton (1330) + TX, Pentoate (631) + TX, Porate (636) + TX, Fosalon (637) + TX, phospholan (1338) + TX, fosmet (638) + TX, phosphamidone (639) + TX, Foxim (642) + TX, pyrimiphos-methyl (652) + TX, polychloroterpenes ( Common name) (1347) + TX, polynactin (alternative name) (653) + TX, proclonol (1350) + TX, propenophos (662) + TX, promasyl (1354) + TX, propargite (671) + TX, Propetamphos (673) + TX, Propoxur (678) + TX, Proticathion (1360) + TX, Protoate (1362) + TX, Pyrethrin I (696) + TX, Pyrethrin II (696) + TX, Pyrethrin (696) + TX, pyridaben (699) + TX, pyridapention (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, Quinal Force (711) + TX, Quintio Force (1381) + TX, R-1492 (Development Code) (1382) + TX, RA-17 (Development Code) (1383) + TX, Rotenone (722) ) + TX, Shuradan (1389) + TX, Cebu Force (alternative name) + TX, Selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, Camimid 1402 + TX , Spirodiclofen (738) + TX, Spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, Sulfiram (alternative name) [CCN] + TX, Sulfluramid ( 750) + TX, Sulfothep (753) + TX, Sulfur (754) + TX, SZI-121 (Development Code) (757) + TX, Tau-fluvalinate (398) + TX, Tebufenpyrad (763) + TX, TEPP (1417) + TX, Terbam (alternative name) + TX, Tetrachlorbinphos (777) + TX, tetradiphone (786) + TX, tetranactin (alternative name) (653) + TX, tetra Tassel(1425) + TX , Thiaphenox (Alternative Name) + TX, Thiocarboxim (1431) + TX, Thiophanox (800) + TX, Thiometone (801) + TX, Thioquinox (1436) + TX, Turingin Ensin ( Alternative name) [CCN] + TX, Triamifos (1441) + TX, Triaraten (1443) + TX, Triazophos (820) + TX, Triazuron (alternative name) + TX, Trichlorphone (824) ) + TX, tripenophos (1455) + TX, trinactin (alternative name) 653 + TX, bamidothione (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX A pesticide selected from the group of substances consisting of,

Betoxazine [CCN] + TX, copper dioctanoate (IUPAC name) 170 + TX, copper sulfate (172) + TX, sibutrin [CCN] + TX, diclones (1052) + TX, dichlorophen ( 232) + TX, endotal (295) + TX, pentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamin (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + Algicide selected from the group consisting of TX,

Abamectin (1) + TX, Cruformate (1011) + TX, Doramectin (Alternative Name) [CCN] + TX, Emamectin (291) + TX, Emamectin Benzoate (291) + TX, Eprnomectin (Alternative Name)[CCN] + TX, Ivermectin (Alternative Name)[CCN] + TX, Milbemycin Oxime (Alternative Name)[CCN] + TX, Moxidectin (Alternative Name)[CCN] + TX, Piperazine Anthelmintics selected from the group of substances consisting of [CCN] + TX, Selamectin (Alternative Name) [CCN] + TX, Spinosad (737) and Thiophanate (1435) + TX,

From the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, pention (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX Chosen stimulants,

1-hydroxy-1 H -pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydr Roxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodicin (1112) + TX, phenaminosulf (1144) + TX, formaldehyde (404) + TX, hydragafen (alternative Name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitra Pyrine (580) + TX, octylinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, teclophthalam (766) + TX, and thiomersal (alternative name) [CCN] + selected from the group of materials consisting of TX Fungicide,

Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. Alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Apelinus Abdomie Aphelinus abdominalis (alternative name)(33) + TX, Aphidius colemani (alternative name)(34) + TX, Aphidoletes aphidimyza (alternative name)(Alternative name)( 35) + TX, Autographa californica NPV (alternative name)(38) + TX, Bacillus firmus (alternative name)(48) + TX, Bacillus spaericos nade ( Bacillus sphaericus Neide (Scientific name)(49) + TX, Bacillus thuringiensis Berliner (Scientific name)(51) + TX, Bacillus thuringiensis subsp.aizawai (Scientific name)(Scientific name) 51) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific) (51) + TX, Bacillus spp N-Sys-to Lindsay Kur Starkey (scientific name) (51) + TX, Bacillus spp tene-to Lindsay N-Sys brioche varnish (Bacillus thuringiensis subsp. tenebrionis) (scientific name) (51) + TX, Rove Beria Bridge Ana (Beauve ria bassiana (alternative name)(53) + TX, Beauveria brongniartii (alternative name)(54) + TX, Chrysoperla carnea (alternative name)(151) + TX, Cryptolaemus montrouzieri (alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica )(Alternative)(212) + TX, diglyphus isaea (Alternative)(254) + TX, Encarsia formosa (Scientific)(293) + TX, Ere Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) 433 + TX, Hippodamia convergens (alternative name) 442 + TX, Leptomastix dactylopii ( Alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, meta Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var. acridum ) (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (Alternative Name)(575) + TX, Orius spp.(Alternative Name)(596) + TX, Pacilomyces Fumosoroseus ( Paecilomyces fumosoroseus (alternative name) (613) + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedral virus (scientific name) )(741) + TX, Steinernema bibionis (Alternative Name)(742) + TX, Steinernema carpocapsae (Alternative Name)(742) + TX, Steinernema Steinernema feltiae (Alternate) (742) + TX, Steinernema glaseri (Alternate) (742) + TX, Steinernema riobrave (Alternate) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema species ( Steinernema spp.) (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844 ) And Verticillium lecanii (Alternate) (848) + TX, Bacillus standing Bacillus subtilis var. amyloliquefaciens ) FZB24 (available from Novozymes Biologicals Inc. (5400 Corporate Circle, Salem, VA 24153, USA) and known under the trade name Taegro®) + biological agent selected from the group of substances consisting of TX,

Soil fungicide selected from the group of substances consisting of iodomethane (IUPAC name) 542 and methyl bromide (537) + TX,

Apollate [CCN] + TX, Bisazir (alternative name) [CCN] + TX, Busulfan (alternative name) [CCN] + TX, Difluvenzuron 250 + TX, Dimatif (alternative name) [CCN ] + TX, Hemel [CCN] + TX, Hempa [CCN] + TX, Metepa [CCN] + TX, Methiotepa [CCN] + TX, Methyl Apolate [CCN] + TX, Morzide [CCN] + TX, Fenfluron (Alternative Name)[CCN] + TX, Tepa[CCN] + TX, Thiophhempa (Alternative Name)[CCN] + TX, Thiotepa (Alternative Name)[CCN] + TX, Tretamine (Alternative Name) [CCN] and uredepa (alternative name) [CCN] + chemical infertility selected from the group of substances consisting of TX,

( E )-Des-5-en-1-yl acetate (IUPAC name) (222) with ( E )-des-5-en-1-ol (222) + TX, ( E )-trides-4-ene- 1-yl acetate (IUPAC name) (829) + TX, ( E )-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, ( E,Z )-tetradeca-4 ,10-dien-1-yl acetate (IUPAC name) (779) + TX, ( Z )-dodes-7-en-1-yl acetate (IUPAC name) (285) + TX, ( Z )-hexades -11-enal (IUPAC name) (436) + TX, ( Z )-hexades-11-en-1-yl acetate (IUPAC name) (437) + TX, ( Z )-hexades-13-en- 11-In-1-yl acetate (IUPAC name) (438) + TX, ( Z )-Icos-13-en-10-one (IUPAC name) (448) + TX, ( Z )-tetrades-7- N-1-al (IUPAC name) (782) + TX, ( Z )-tetrades-9-en-1-ol (IUPAC name) (783) + TX, ( Z )-tetrades-9-en- 1-yl acetate (IUPAC name) (784) + TX, (7 E ,9 Z )-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9 Z ,11 E )-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9 Z ,12 E )-tetradeca-9,12-dien-1-yl acetate (IUPAC name) ) (781) + TX, 14-methyloctades-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544 ) + TX, alpha-multistriatine (alternative name) [CCN] + TX, brevicomin (alternative name) [CCN] + TX, Kodlerure (alternative name) [CCN] + TX, cordlemon (alternative name) ) (167) + TX, Cuelure (alternative name) (179) + TX, Disparule (277) + TX, dodes-8-en-1-yl acetate (IUPAC name) (286) + TX, Dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodeca-8 + TX, 10-diene-1 -Yl acetate (IUPAC name) (284) + TX, Dominicallure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, Frontalin (alternative name) [CCN] + TX, Koshiflure (alternative name) 420 + TX, Grandleure 421 + TX, Grandleure I (alternative name) (421 ) + TX, Grandleure II (alternative name) 421 + TX, Grandleure III (alternative name) 421 + TX, Grandleure IV (alternative name) 421 + TX, Hexalure[ CCN] + TX, ifsdinol (alternative name) [CCN] + TX, ifensol (alternative name) [CCN] + TX, zaponilure (alternative name) (481) + TX, lineine (alternative name) [CCN] + TX, Little Lure (alternative name) [CCN] + TX, Luflure (alternative name) [CCN] + TX, Madeleure [CCN] + TX, Megatomosan (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalore (563) + TX, octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, octadeca- 3,13-dien-1-yl acetate (IUPAC name) (589) + TX, Orphralure (alternative name) [CCN] + TX, Oritaltale (alternative name) 317 + TX, Ostramon (alternative) Name)[CCN] + TX, Cygure[CCN] + TX, Sordidine (Alternative Name)(736) + TX, Sulcatol (Alternative Name)[CCN] + TX, Tetrades-11-en-1-yl Acetate (IUPAC name) (785) + TX, Trimedleure (839) + TX, Trimedleure A (alternative name) (839) + TX, Trimedleure B ₁ (alternative name) (839) + From the group of substances consisting of TX, Trimedleure B ₂ (alternative name) 839 + TX, Trimedleure C (alternative name) 839 and Trunk-Cole (alternative name) [CCN] + TX Selected insect pheromone,

2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy (polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN ] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridine [ CCN] + insect repellent selected from the group of substances consisting of TX,

1-dichloro-1-nitroethane (IUPAC/chemical abstract name) (1058) + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), + TX, 1,2-dichloropropane (IUPAC/chemical abstract name) 1062 + TX, 1,2-dichloropropane (IUPAC name) with 1,3-dichloropropene (1063) + TX, 1-bromo-2 -Chloroethane (IUPAC/chemical abstract name) (916) + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name) (1451) + TX, 2,2 -Dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (IUPAC name) (1066) + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate (IUPAC/chemical abstract) (1109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/chemical abstract) (935) + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl) Phenyl methylcarbamate (IUPAC/chemical abstract name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986) + TX, 2-chlorovinyl diethyl Phosphate (IUPAC name) (984) + TX, 2-Imidazolidone (IUPAC name) (1225) + TX, 2-isovaleryldan-1,3-dione (IUPAC name) (1246) + TX, 2 -Methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo- 1-Chloroprop-1-ene (IUPAC name) (917) + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283) + TX, 4-methyl( Prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPAC Name)(1085) + TX, Abamectin(1) + TX, Acetate(2) + TX, Acetamiprid(4) + TX, Acethion (Alternative Name)[CCN] + TX, Acetoprole[CCN] + TX, Acrinatrin (9) + TX, Acrylonitrile (IUPAC name) (861) + TX, Alanicarb (15) + TX, Aldicarb (16) + TX, Aldoxycarb (863) + TX, Aldrin (864) + TX, aletrin (17) + TX, allosamidine (alternative name) [CCN] + TX, alixicarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ex Disson (alternative name) [CCN] + TX, aluminum phosphide (640) + TX, amidionion (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amitone (875) + TX, Amitone Hydrogen Oxalate (875) + TX, Amitraz (24) + TX, Anavacin (877) + TX, Atidathione (883) + TX, AVI 382 (Compound Code) + TX, AZ 60541 (Compound Code) + TX, Azadiractin (Alternative Name) (41) + TX, Azametiphos (42) + TX, Azinphos-ethyl (44) + TX, Azinphos-methyl (45 ) + TX, azotoate (889) + TX, Bacillus thuringiensis delta endotoxin (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (IUPAC / Chemical abstract name) (892) + TX, Barthrin [CCN] + TX, Bayer 22/190 (development code) (893) + TX, buyer 22408 (development code) (894) + TX, Vendio Carb(58) + TX, Benfuracarb(60) + TX, Bensultop(66) + TX, Beta-cyfluthrin(194) + TX, Beta-cypermethrin(203) + TX, Bifenthrin (76) + TX, Bioalthrin (78) + TX, Bioalthrin S -cyclopentenyl isomer (alternative name)(79) + TX, Bioethanomethrin [CCN] + TX, Biopermethrin (908) + TX, bioresmethrin (80) + TX, bis(2-chloroethyl) ether (IUPAC name) (909) + TX, bistriflurone (83) + TX, borax (86) + TX, brofenvale Rate (alternative name) + TX, Brompenbin Force (914) + TX, bromocycline (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb ( 924) + TX, Bupropezin (99) + TX, Butacarb (926) + TX, Butathiophos (927) + TX, Butocarboxim (103) + TX, Butonate (932) + TX, Bu Toxycarboxim (104) + TX, butyl pyridaben (alternative name) + TX, kadusaphos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (111) + TX, camphorchlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (IUPAC/chemistry) Abstract name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbophenotion (947) + TX, carbosulfane (119) + TX, cartap (123) + TX, Kar Top hydrochloride (123) + TX, sebadine (alternative name) (725) + TX, chlorbisiclene (960) + TX, chlordan (128) + TX, chlordecon (963) + TX, chlordimeform ( 964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyphos (129) + TX, chlorfenapyr (130) + TX, chlorfenbinphos (131) + TX, chlorfluazuron (132) ) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorpoxim (989) + TX, chlorprazophos (990) + TX, chlorpyriphos (145) ) + TX, chlorpyriphos-methyl (146) + TX, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, Cineline (696) + TX, Cis-Resmetrin (alternative name) + TX, Cismetrin (80) + TX, Clocitrin (alternative name) + TX, Cloetocarb (999) + TX, Closantel (Alternative Name) [CCN] + TX, Clotianidin (165) + TX, Copper Acetoarsenite [CCN] + TX, Copper Arsenate [CCN] + TX, Copper Oleate [CCN] + TX, Koumafoss (174) + TX, Koomitoate (1006) + TX, Crotamiton (Alternative Name) [CCN] + TX, Crothoxyphos (1010) + TX, Crepo Mate (1011) + TX, Cryolite (Alternate Name) (177) + TX, CS 708 (Development Code) (1012) + TX, Cyanophenphos (1019) + TX, Cyanophos (184) + TX, Cyan Toeate (1020) + TX, cyclethrin [CCN] + TX, cycloprotrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, Cyphenothrin (206) + TX, Cyromazine (209) + TX, Citiate (Alternative Name) [CCN] + TX, d -Limonene (Alternative Name) [CCN] + TX, d -Tetra Metrin (Alternative) (788) + TX, DAEP (1031) + TX, Dazomet (216) + TX, DDT (219) + TX, Decarbofuran (1034) + TX, Deltamethrin (223) + TX, Demethion(1037) + TX, Demethion-O(1037) + TX, Demethion-S(1037) + TX, Demethone(1038) + TX, Demethone-methyl(224) + TX , Demetone-O(1038) + TX, Demetone-O-methyl(224) + TX, Demetone-S(1038) + TX, Demetone-S-methyl(224) + TX, Demetone-S- Methylsulfone (1039) + TX, Diafenthiuron (226) + TX, Diallyphos (1042) + TX, Diamidase (1044) + TX, Diazinon (227) + TX, Dicaptone (1050) + TX , Diclopention (1051) + TX, Dichlorbose (236) + TX, Diclifos (Alternative Name) + TX, Dicresyl (Alternative Name) [CCN] + TX, Dicrotoforce (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + T X, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076) + TX, difluvenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN ] + TX, Dimepox (1081) + TX, Dimethane (1085) + TX, Dimethoate (262) + TX, Dimethrin (1083) + TX, Dimethylvinphos (265) + TX, Dimethyllan (1086) ) + TX, Dinex(1089) + TX, Dinex-Declexin(1089) + TX, Dinoprof(1093) + TX, Dinosam(1094) + TX, Dinoseb(1095) + TX, Dinote Furan (271) + TX, Diphenolan (1099) + TX, Dioxabenzophos (1100) + TX, Dioxacarb (1101) + TX, Dioxathion (1102) + TX, Disulfotone (278) + TX, Dtycroforce (1108) + TX, DNOC (282) + TX, Doramectin (Alternative Name) [CCN] + TX, DSP (1115) + TX, Ecdysterone (Alternative Name) [CCN] + TX, EI 1642 (development code) (1118) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1120) + TX, empentrin (292) + TX, endosulfan (294) + TX, endothion (1121) + TX, endrin (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epofenonan (1124) + TX, eprinomectin (alternative name)[ CCN] + TX, Espenvalerate (302) + TX, Etafos (alternative name) [CCN] + TX, Ethiophene Carb (308) + TX, Ethion (309) + TX, Etiprole (310) + TX, Ethoate-methyl (1134) + TX, Etopropos (312) + TX, ethyl formate (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylene di Bromide (316) + TX, Ethylene Dichloride (chemical name) (1136) + TX, Ethylene Oxide [CCN] + TX, Etopenrox (319) + TX, Ethrimphos (1142) + TX, EXD(1143) + TX, Pamppur(323) + TX, Penamifos(326) + TX, Penajaflor(1147) + TX, Penchlorfos(1148) + TX, Penetacarb(1149) + TX, fenfluthrin (1150) + TX, phenytrothion (335) + TX, phenobucarb (336) + TX, phenoxa cream (1153) + TX, phenoxycarb (340) + TX, Penpyridine (1155) + TX, Penpropartrine (342) + TX, Penpyrad (alternative name) + TX, Pensulpotion (1158) + TX, Penthion (346) + TX, Penthion-ethyl[ CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (CAS. Registration number: 272451-65-7) + TX, flucofuron (1168) + TX, flucycloxuron (366) + TX, flucilinate (367) + TX, fluenetyl (1169) + TX, Flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development Code) (1185) + TX, phonophos (1191) + TX, formatenate (405) + TX, formethanate hydrochloride (405) + TX, formothion (1192) + TX, formparanate (1193) ) + TX, phosmethyllan (1194) + TX, phosphite (1195) + TX, postasetite (408) + TX, postistane (1196) + TX, furiocarb (412) + TX, Purethrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guavatin (422) + TX, guavatin acetate (422) + TX, GY- 81 (Development Code) (423) + TX, Halfenprox (424) + TX, Halopenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, Heptachlor (1211) + TX , Heptenophos (432) + TX, Heterophos [CCN] + TX, Hexaflumuron (439) + TX, HHDN (864) + TX, Hydramethylnon (443) + TX, Hydrogen cyanide (444) + TX, Hydroprene (445) + TX, High Queen Carb (1223) + TX, Imidacloprid (458) + TX, Imiprotrin (460) + TX, Indoxacarb (465) + TX, Iodo Methane (IUPAC name) (542) + TX, IPSP (1229) + TX, Isazophos (1231) + TX, Isobenzone (1232) + TX, Isocarbophos (Alternative Name) (473) + TX, Iso DRIN (1235) + TX, Isophenphos (1236) + TX, Isolan (1237) + TX, Isoprocarb (472) + TX, Isopro Phil O -(methoxyaminothiophosphoryl) salicylate (IUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX , Ivermectin (Alternative Name) [CCN] + TX, Jasmoline I (696) + TX, Jasmoline II (696) + TX, Zodfenphos (1248) + TX, Larva Hormone I (Alternative Name) [CCN ] + TX, Larva Hormone II (Alternative Name) [CCN] + TX, Larva Hormone III (Alternative Name) [CCN] + TX, Keleban (1249) + TX, Kinoprene (484) + TX, Lambda-Saihal Lotrine (198) + TX, Lead Arsenate [CCN] + TX, Lepimectin (CCN) + TX, Leptophos (1250) + TX, Lyndan (430) + TX, Lyrimpos (1251) + TX, Loupe Nuron (490) + TX, ritidathione (1253) + TX, m -cumenyl methylcarbamate (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malathion ( 492) + TX, Malonoben (1254) + TX, Magidox (1255) + TX, Mecarbaum (502) + TX, Mecarphone (1258) + TX, Menazone (1260) + TX, Mephospolan (1261) ) + TX, Mercury Chloride (513) + TX, Mesulfenphos (1263) + TX, Metaflumizone (CCN) + TX, Metham (519) + TX, Metham-Potassium (Alternative Name) (519) + TX, Metham-Sodium (519) + TX, Metacripos (1266) + TX, Metamidosphos(527) + TX, Methanesulfonyl Fluoride (IUPAC/Chemical Abstract) (1268) + TX, Methitathione (529) + TX, Methiocarb (530) + TX, Metocrotophos (1273) + TX, Metomil (531) + TX, Metoprene (532) + TX, Metoquin-butyl (1276) + TX, methotrin (alternative name) (533) + TX, methoxycyclo (534) + TX, methoxyphenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) ) + TX, Methylchloroform (Alternative Name) [CCN] + TX, Methylene Chloride [CCN] + TX, Metofluthrin [CCN] + TX, Metholcarb (550) + TX, Metoxadiazone (1288) + TX, Mevin Force (556) + TX, mexacarbate (1290) + TX, Milbemectin (557) + TX, Milbemycin Oxime (alternative name) [CCN] + TX, Mifapox (1293) + TX, Mirex (1294) + TX, Monocrotophos (561) + TX, Morphothion (1300) + TX, Moxidectin (alternative name) [CCN] + TX, Naphthalophos (alternative name) [CCN] + TX, Naled (567 ) + TX, naphthalene (IUPAC/chemical abstract name) 1303 + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyram (579) + TX, nithiazine (1311) + TX, nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc Chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (common name) (1319) + TX, novaluron (585) + TX, nobiflu Muron (586) + TX, O -5-dichloro-4-iodophenyl O -ethyl ethylphosphonothioate (IUPAC name) (1057) + TX, O,O -diethyl O -4-methyl-2- Oxo- 2H -chromen-7-yl phosphorothioate (IUPAC name) (1074) + TX, O,O -diethyl O -6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075) + TX, O , O, O ', O' - tetrapropyl dt operational with phosphate (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, Ome Sat benzoate (594) + TX, oxamyl (602) + TX, oxydemetone-methyl (609) + TX, oxydepropos (1324) + TX, oxydisulfotone (1325) + TX, pp'-DDT( 219) + TX, Para -Dichlorobenzene [CCN] + TX, Parathion (615) + TX, Parathion-methyl (616) + TX, Penflurone (Alternative Name) [CCN] + TX, Pentachlorophenol (623) + TX, Pentachlorophenyl Laurate (IUPAC name) (623) + TX, Permethrin (626) + TX, Petroleum Oil (Alternative Name) (628) + TX, PH 60-38 (Development Code) (1328) + TX, Pencapton (1330) + TX, Phenotrin (630) + TX, Pentoate (631) + TX, Porate (636) + TX, Fosalon (637) + TX, Phospholan (1338) + TX, Fosmet (638) + TX, phosnichlor (1339) + TX, phosphamidone (639) + TX, phosphine (IUPAC name) (640) + TX, Foxim (642) + TX, Foxim-methyl (1340) + TX, pyrimeta Force (1344) + TX, pyrimicarb (651) + TX, pyrimiphos-ethyl (1345) + TX, pyrimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomer (IUPAC name) (1346) + TX, polychloroterpenes (common name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, praletrin (655) + TX, precocene I (Alternative Name) [CCN] + TX, Precosen II (Alternative Name) [CCN] + TX, Precocene III (Alternative Name) [CCN] + TX, Pyrimidophos (1349) + TX, Propenophos ( 662) + TX, Profluthrin [CCN] + TX, Promacil (1354) + TX, Promecarb (1355) + TX, Propaphos (1356) + TX, Propetamphos (673) + TX, Pro Foxur (678) + TX, Proticathion (1360) + TX, Prothiophos (686) + TX, Protoate (1362) + TX, Protrippenbutt [CCN] + TX, Pymetrozine (688) + TX, pyraclophos (689) + TX, pyrazophos (693) + TX, pyrethmeline (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX , Pyrethrin (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, pyridafenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, Pyridoxyphen (708) + TX, Quacia (Alternative Name) [CCN] + TX, Quinal Force (711) + TX, Quinal Force-methyl (1376) + TX, Quinothion (1380) + TX , Quintioforce (1381) + TX, R-1492 (development code) (1382) + TX, Lapoxanide (alternative name) [CCN] + TX, Resmethrin (719) + TX, Rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, liana (alternative name) (1387) + TX, rianodine (common name) (1387) + TX, Sabadilla (Alternative Name)(725) + TX, Shuradan(1389) + TX, Cebufos(Alternative Name) + TX, Selamectin(Alternative Name)[CCN] + TX, SI-0009(Compound Code) + TX , SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluorene (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (IUPAC/chemical abstract) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium penta Chlorophenoxide (623) + TX, sodium selenate (IUPAC name) 1401 + TX, sodium thiocyanate [CCN] + TX, sofa mid 1402 + TX, spinosad (737) + TX, spiromesh Pen (739) + TX, Spirottremat (CCN) + TX, Sulfurfuron (746) + TX, Sulfurfuron-Sodium (746) + TX, Sulfluramid (750) + TX, Sulfothep (753) + TX, Sulfuryl Fluoride (756) + TX, Sulpropos(1408) + TX, Tar Oil (Alternate Name) 758 + TX, Tau-fluvalinate (398) + TX, Tajimcarb (1412) + TX, TDE (1414) + TX, Tebufenozide (762) + TX, Tebufenpyrad (763) + TX, Tebufirimphos (764) + TX, Tefluben Juron (768) + TX, Tefluthrin (769) + TX, Temepos (770) + TX, TEPP (1417) + TX, Teraletrin (1418) + TX, Terbam (alternative name) + TX, Terre Buphos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid ( 791) + TX, Thiaphenox (alternative name) + TX, Thiamethoxam (792) + TX, Ticrophos (1428) + TX, Thiocarboxim (1431) + TX, Thiocyclam (798) + TX , Thiocyclam Hydrogen Oxalate (798) + TX, Thiodicarb (799) + TX, Thiophanox (800) + TX, Thiometone (801) + TX, Thionazine (1434) + TX, Thiosultop ( 803) + TX, Thiosultop-Sodium (803) + TX, Turingensin (Alternative Name) [CCN] + TX, Tolfenpyrad (809) + TX, Tralomethrin (812) + TX, Transfluthrin ( 813) + TX, transfermethrin (1440) + TX, triamifos (1441) + TX, triamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, tri Chlorphone (824) + TX, Trichlormetaphos-3 (alternative name) [CCN] + TX, Trichloronath (1452) + TX, Trifenophos (1455) + TX, Triple Lumuron (835) + TX , Trimetacarb (840) + TX, Triprene (1459) + TX, Bamidothione (847) + TX, Vaniliprole [CCN] + TX, Veratridine (alternative name) (725) + TX, Beratrin (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zeta Metrin (alternative Name) + TX, zinc phosphide (640) + TX, zolapropos (1469) and ZXI 8901 (development code) 858 + TX, cyantraniliprole [736994-63-19 + TX, chloranthra Niliprole[500008-45-7] + TX, Sienopyrafen[560121-52-0] + TX, Cyflumetofen[400882-07-7] + TX, Pyrifluquinazone[337458-27 -2] + TX, Spinetoram[187166-40-1 + 187166-15-0] + TX, Spirotetramat[203313-25-1] + TX, Sulfoxaflor[946578-00-3] + TX , Flupiprole[704886-18-0] + TX, meperfluthrin[915288-13-0] + TX, tetramethyl fluthrin[84937-88-2] + TX, triflumezopyrim (WO 2012/ Insecticide selected from the group of substances consisting of + TX),

Bis(tributyltin)oxide (IUPAC name) (913) + TX, Bromoacetamide [CCN] + TX, Calcium Arsenate [CCN] + TX, Chloerocarb (999) + TX, Copper Acetoar Senite [CCN] + TX, copper sulfate (172) + TX, pentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, Tajimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, tripenmorph (1454) + TX, trimetacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprol [394730-71-3] + a mollusc agent selected from the group of substances consisting of TX,

AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC/chemical abstract name) (1045) + TX, 1,2-dichloropropane (IUPAC/chemical abstract name) (1062 ) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydroty Offen, 1,1-dioxide (IUPAC/chemical abstract name) (1065) + TX, 3-(4-chlorophenyl)-5-methyllodanine (IUPAC name) (980) + TX, 5-methyl-6- Thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, Acetoprole [CCN] + TX, Alanicarb (15) + TX, Aldicarb (16) + TX, Aldoxicarb (863) + TX, AZ 60541 (Compound Code) + TX, Benqlo Thiaz [CCN] + TX, Benomyl (62) + TX, Butyl pyridaben (alternative name) + TX, Kadusaphos (109) + TX, Carbofuran (118) + TX, Carbon disulfide (945) + TX , Carbosulfane (119) + TX, chloropicrin (141) + TX, chlorpyriphos (145) + TX, chlorotocarb (999) + TX, cytokinin (alternative name) 210 + TX, dazo Met (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, Diamidafos (1044) + TX, Diclofenthion (1051) + TX, Diclipos (alternative name) + TX, Dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, Etopropos(312) + TX, Ethylene dibromide(316) + TX, Fenamiphos(326) + TX, Penpyrad(Alternative name) + TX, Pensulpotion(1158) + TX, Postase T (408) + TX, Postietan (1196) + TX, Purfural (alternative name) [C CN] + TX, GY-81 (Development Code) (423) + TX, HeteroForce [CCN] + TX, Iodomethane (IUPAC name) (542) + TX, Isamido Force (1230) + TX, Isazo Force (1231) + TX, Ivermectin (Alternate Name) [CCN] + TX, Kinetic (Alternate Name) 210 + TX, Mecarphone (1258) + TX, Metham (519) + TX, Metham-Potassium ( Alternative name) (519) + TX, Metham-Sodium (519) + TX, Methyl bromide (537) + TX, Methyl isothiocyanate (543) + TX, Milbemycin oxime (Alternative name) [CCN] + TX, Moxidectin (Alternative Name) [CCN] + TX, Myrothecium verrucaria Composition (Alternative Name) (565) + TX, NC-184 (Compound Code) + TX, Oxamyl (602) + TX, Forrate (636) + TX, Phosphamidone (639) + TX, Phosphocarb [CCN] + TX, Cebufos (alternative name) + TX, Selamectin (alternative name) [CCN] + TX, Spinosad (737) + TX, Terbam (alternative name) + TX, Terbuphos (773) + TX, tetrachlorothiophene (IUPAC/chemical abstract name) (1422) + TX, Thiaphenox (alternative name) + TX , Thionazine (1434) + TX, Triazophos (820) + TX, Triazuron (alternative name) + TX, Xylenols [CCN] + TX, YI-5302 (compound code) and Zeatin (alternative name) (210) + TX, fluenesulfone [318290-98-1] + a nematode selected from the group of substances consisting of TX,

A nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin 580 + TX,

With acibenzolar (6) + TX, acibenzolar- S -methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX Plant activators selected from the group of substances consisting of,

2-isovaleric end-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, alpha-chloro high DRINN [CCN] + TX, aluminum phosphide (640) + TX, anthoc (880) + TX, arsenic oxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, Brody Pacomum (89) + TX, Bromadiolone (91) + TX, Brometallin (92) + TX, Calcium Cyanide (444) + TX, Chloralose (127) + TX, Chloropathinone (140) + TX, cholecalciferol (alternative name) (850) + TX, comumachlor (1004) + TX, comumafuryl (1005) + TX, commateralyl (175) + TX, creamydin (1009) + TX, Difenacomum (246) + TX, Difetialone (249) + TX, Difacinone (273) + TX, Ergocalciferol (301) + TX, Plocoumafen (357) + TX, Fluoroacetamide (379) + TX, flupropadidine (1183) + TX, flupropadidine hydrochloride (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide ( 444) + TX, iodomethane (IUPAC name) (542) + TX, lindan (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide ( 1318) + TX, posase team (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindon (1341) + TX, potassium arsenite [CCN] + TX, flute Nuron (1371) + TX, sililoside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoro-acetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + a stimulant selected from the group of substances consisting of TX,

2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, Farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX , Piperonyl butoxide (649) + TX, piperotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) 724 + TX, sesamex (1393) + TX, sessas A synergist selected from the group of substances consisting of moline (1394) and sulfoxide (1406) + TX,

Anthraquinone (32) + TX, Chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) )(1069) + TX, Guazatin(422) + TX, Guazatin Acetate(422) + TX, Methiocarb(530) + TX, Pyridin-4-amine (IUPAC name)(23) + TX , Animal repellent selected from the group of materials consisting of thyram (804) + TX, trimetacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,

A viral eradication agent selected from the group of substances consisting of Imanine (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX

A wound protectant selected from the group of materials consisting of mercuric oxide mercury (512) + TX, octylinone (590) and thiophanate-methyl (802) + TX, and

Amethoxtradine [865318-97-4] + TX, amisulbrom [348635-87-0] + TX, azaconazole [60207-31-0] + TX, benzobindiflupyr [1072957-71-1 ] + TX, Vitertanol [70585-36-3] + TX, Bixafen[581809-46-3] + TX, Bromuconazole[116255-48-2] + TX, Comoxistrobin[850881-70 -8] + TX, ciproconazole[94361-06-5] + TX, diphenoconazole[119446-68-3] + TX, diniconazole[83657-24-3] + TX, enoxastrobin[ 238410-11-2] + TX, Epoxyconazole[106325-08-0] + TX, Penbuconazole[114369-43-6] + TX, Penpyrazamine[473798-59-3] + TX, Fluquin Conazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674-21-0] + TX, fluxapiroxad [907204-31-3] + TX, fluopyram[658066-35-4] + TX, phenaminestrobin[366815-39-6] + TX, isofetamide[875915-78-9] + TX, hexaconazole[79983-71-4 ] + TX, Imazalyl[35554-44-0] + TX, Imibenconazole[86598-92-7] + TX, Ipconazole[125225-28-7] + TX, Ipfentrifluconazole[1417782-08- 1] + TX, isotianil [224049-04-1] + TX, mandestrobin [173662-97-0] (can be prepared according to the procedures described in WO 2010/093059) + TX, Mefentri Fluconazole [1417782-03-6] + TX, Metconazole [125116-23-6] + TX, Miklobutanyl [88671-89-0] + TX, Paclobutrazol [76738-62-0] + TX, Pepurazoate[101903-30-4] + TX, Fenflufen[494793-67-8] + TX, Fenconazole[66246-88-6] + TX, Prothioconazole[178928-70 -6] + TX, Pipehenox[88283-41- 4] + TX, prochloraz[67747-09-5] + TX, propiconazole[60207-90-1] + TX, cimeconazole[149508-90-7] + TX, tebuconazole[107534- 96-3] + TX, tetraconazole[112281-77-3] + TX, triadimephone[43121-43-3] + TX, triadimenol[55219-65-3] + TX, triflumisol[ 99387-89-0] + TX, Triticonazole [131983-72-7] + TX, Ansimidol [12771-68-5] + TX, Penarimol [60168-88-9] + TX, Noari Mall [63284-71-9] + TX, volumetric mate [41483-43-6] + TX, dimetirimol [5221-53-4] + TX, etirimol [23947-60-6] + TX, dodemor Pro[1593-77-7] + TX, fenpropidin[67306-00-7] + TX, fenpropimorph[67564-91-4] + TX, Spiroxamine [118134-30-8] + TX , Tridemorph[81412-43-3] + TX, Ciprodinil[121552-61-2] + TX, Mepanipyrim[110235-47-7] + TX, Pyrimethanil[53112-28-0 ] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [131341-86-1] + TX, fluindapyr[1383809-87-7] + TX, benalaxyl [71626- 11-4] + TX, furalaxyl[57646-30-7] + TX, metalaxyl[57837-19-1] + TX, R-metalaxyl[70630-17-0] + TX, ofoprace[58810- 48-3] + TX, Oxadixyl[77732-09-3] + TX, Benomyl[17804-35-2] + TX, Carbendazim[10605-21-7] + TX, Devacarb[62732-91 -6] + TX, fuberidazole [3878-19-1] + TX, thiavendazole [148-79-8] + TX, clozolinate [84332-86-5] + TX, diclozoline [24201 -58-9] + TX, Iprodione [36734-19-7] + TX, Miclozoline [54864-61-8] + TX, Procymidone [32809-16-8] + TX, Vinclozoline [50471-44-8] + TX, Boscalid [188425-85-6] + TX, Carboxine [5234-68-4] + TX, Fenfuram [24691-80-3] + TX, Plutolanyl [66332-96-5] + TX, Plutianil [958647-10-4] + TX, Mepronil [55814-41-0] + TX, Oxycarboxin[5259-88-1] + TX, Penthiopyrad[183675-82-3] + TX, Thifluzamide[130000-40-7] + TX, Guazatine[108173-90 -6] + TX, dodine [2439-10-3] [112-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8 ] + TX, dimoxystrobin [149961-52-4] + TX, enestrobin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1 , 93} + TX, fluoxastrobin[361377-29-9] + TX, creoxime-methyl[143390-89-0] + TX, metominostrobin[133408-50 -1] + TX, triple oxystrobin[141517-21-7] + TX, orisastrobin[248593-16-0] + TX, picoxystrobin[117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, pyraoxystrobin[862588-11-2] + TX, Ferbam[14484-64-1] + TX, Mancozeb[8018-01-7] + TX, Maneb[ 12427-38-2] + TX, Methiram[9006-42-2] + TX, Propineb[12071-83-9] + TX, Tiram[137-26-8] + TX, Zineb[12122-67- 7] + TX, Jiram[137-30-4] + TX, Captapol[2425-06-1] + TX, Captan[133-06-2] + TX, Diclofluanid[1085-98-9 ] + TX, fluoroimide [41205-21-4] + TX, polpet [133-07-3] + TX, tolyl fluanid [731-27-1] + TX, Bordeaux mixture [8011-63- 0] + TX, copper hydroxide [20427-59-2] + TX, copper oxide cyclolide [1332-40-7] + TX, copper sulfat [7758-98-7] + TX, copper oxide [1317 -39-1] + TX, Mancopher [53988-93-5] + TX, Auxin-copper [10380-28-6] + TX, Dinocap [131-72-6] + TX, Nitrotal-isopropyl [10552-74-6] + TX, Edifenphos [17109-49-8] + TX, Iprobenfoss [26087-47-8] + TX, Isoprothiolane [50512-35-1] + TX, Force Diphen[36519-00-3] + TX, pyrazophos[13457-18-6] + TX, tolclofos-methyl[57018-04-9] + TX, acibenzolar-S-methyl[135158-54 -2] + TX, anilazine [101-05-3] + TX, Ventiavaliccarb [413615-35- 7] + TX, blasticidin-S[2079-00-7] + TX, kinomethionat[2439-01-2] + TX, chloronep[2675-77-6] + TX, chlorotalonyl [1897-45-6] + TX, Cyflufenamide [180409-60-3] + TX, Simoxanil [57966-95-7] + TX, Diclonal [117-80-6] + TX, Diclo Cimet[139920-32-4] + TX, Diclomezin[62865-36-5] + TX, Dichloran[99-30-9] + TX, Dietophencarb[87130-20-9] + TX, Dimethomorph[110488-70-5] + TX, SYP-LI90 (Plumorph)[211867-47-9] + TX, Dithianon[3347-22-6] + TX, Ethaboxam[162650 -77-3] + TX, Etridiazol[2593-15-9] + TX, Pamoxamone[131807-57-3] + TX, Phenamidone[161326-34-7] + TX, Phenoxanyl[ 115852-48-7] + TX, Pentin [668-34-8] + TX, Ferimzone [89269-64-7] + TX, Fluazinam [79622-59-6] + TX, Fluopicolide [239110 -15-7] + TX, flusulfamide [106917-52-6] + TX, phenhexamid [126833-17-8] + TX, fosetyl-aluminum [39148-24-8] + TX, hymexazole [10004-44-1] + TX, iprovaliccarb [140923-17-7] + TX, IKF-916 (cyazofamide) [120116-88-3] + TX, kasugamycin [6980-18 -3] + TX, metasulfocarb [66952-49-6] + TX, methraphenone [220899-03-6] + TX, pencicuron [66063-05-6] + TX, phthalide [27355- 22-2] + TX, picardbutrax[500207-04-5] + TX, polyoxin[11113-80-7] + TX, probenazole[27605-76-1] + TX, propamocarb [25606-41-1] + TX, Proquinazide [189278-12-4] + TX, Pidiflumetofen [1228284-64- 7] + TX, pyrametostrobin[915410-70-7] + TX, pyroquilon[57369-32-1] + TX, pyriophenone[688046-61-9] + TX, pyribencarb[799247 -52-2] + TX, pyrisoxazole [847749-37-5] + TX, quinoxyfen [124495-18-7] + TX, quintogen [82-68-8] + TX, sulfur [7704- 34-9] + TX, Timorex Gold ^TM (Plant extract containing tea tree oil from Stockton Group) + TX, Tebufloquin [376645-78-2] + TX, Tiadinil [223580-51-6] + TX, tria side [72459-58-6] + TX, tolprocarb [911499-62-2] + TX, triclopyricarb [902760-40-1] + TX, tricyclazole [41814 -78-2] + TX, triporine [26644-46-2] + TX, validamycin [37248-47-8] + TX, baliphenate [283159-90-0] + TX, zoxamide (RH7281) [156052-68-5] + TX, mandipropamide [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, phenacrylac + TX, cedaxic acid [874967-67 -6] + TX, trinexapak-ethyl [95266-40-3] + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1, 2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide (disclosed in WO 2007/048556) + TX, 3-difluoromethyl-1-methyl-1H- Pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide (disclosed in WO 2006/087343) + TX, [(3 S ,4 R ,4a R ,6 S ,6a S ,12 R ,12a S ,12b S )-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a ,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)- 2 H ,11 H naphtho[2,1- b ] pyrano[3,4- e ]pyran-4-yl]methyl-cyclopropanecarboxylate[915972-17-7] + TX and 1,3,5-trimethyl-N-(2-methyl-1 -Oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H- A biologically active compound selected from the group consisting of pyrazole-4-carboxamide [926914-55-8] + TX,

Or N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (Can be prepared according to the procedure described in WO 2010/130767) + TX, 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c' ]Dipyrrole-1,3,5,7(2H,6H)-Tetrone (can be prepared according to the procedure described in WO 2011/138281) + TX, 6-ethyl-5,7-dioxo- Pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N- (2-Chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (can be prepared according to the procedure described in WO 2012/031061) + TX, 3-(difluoro Romethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide (WO 2012/084812) Can be prepared according to) + TX, CAS 850881-30-0 + TX, 3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole 1,1 -Dioxide (can be prepared according to the procedure described in WO 2007/129454) + TX, 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl -Acetamide + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone (prepared according to the procedure described in WO 2005/070917) Can be) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol (described in WO 2011/081174 It can be prepared according to the procedure) + TX, 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2- All (can be prepared according to the procedures described in WO 2011/081174) + TX, oxathiapiproline + TX[1003318-67-9], tert-butyl N-[6-[[[(1-methyl Tetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyri Dill]carbamate + TX, N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (as described in WO 2007/072999) Can be prepared according to the procedure) + TX, 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-car Copyimide (can be prepared according to the procedures described in WO 2014/013842) + TX, 2,2,2-trifluoroethyl N-[2-methyl-1-[[(4-methylbenzoyl)amino ]Methyl]propyl]carbamate + TX, (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-1-(1H-1, 2,4-triazol-1-yl)propan-2-ol + TX, (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl] -3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl -1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl ]Pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-( 4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (can be prepared according to the procedure described in WO 2007/031513) ) + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazole- 4-day]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate (can be prepared according to the procedure described in WO 2012/025557) + TX, boot- 3-Inyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (WO 2010/000841 Can be prepared according to the procedures described in the heading) + TX, 2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]- 4H-1,2,4-triazole-3-thione (WO 2010/1460 Can be prepared according to the procedure described in No. 31) + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl] Carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (can be prepared according to the procedures described in WO 2005/121104 ) + TX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (WO 2013/024082) Can be prepared according to the procedures described in) + TX, 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (as described in WO 2012/020774) Can be prepared according to the procedure) + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile (WO 2012/020774) It can be prepared according to) + TX, ( R )-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide (Can be prepared according to the procedure described in WO 2011/162397) + TX, 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl )-1-methyl-pyrazole-4-carboxamide (can be prepared according to the procedure described in WO 2012/084812) + TX, 1-[2-[[1-(4-chlorophenyl)pyra Sol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (can be prepared according to the procedure described in WO 2013/162072) + TX, 1-methyl -4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one (WO 2014/ Can be prepared according to the procedures described in 051165) + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N, 3-dimethyl-pent-3-enamide + TX, (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX, N-(5-chloro-2-isopropyl Benzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl Pyrazole-4-carboxamide [1255734-28-1] (can be prepared according to the procedures described in WO 2010/130767) + TX, 3-(difluoromethyl)-N-[(R) -2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazole-4-carboxamide[1352994-67-2] + TX, N'-( 2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichloro-thiazol-2-yloxy)- 2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-form Amidine + TX, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX,

(펜피콕사미드[517875-34-2]) + TX(WO 2003/035617호에 기술된 바와 같음), (1S)-2,2-비스(4-플루오로페닐)-1-메틸에틸 N-{[3-(아세틸옥시)-4-메톡시-2-피리딜]카르보닐}-L-알라니네이트[1961312-55-9] (WO 2016/122802호에 기술된 바와 같은 플로릴피콕사미드) + TX, 2-(디플루오로메틸)-N-(1,1,3-트리메틸인단-4-일)피리딘-3-카르복사미드 + TX, 2-(디플루오로메틸)-N-(3-에틸-1,1-디메틸-인단-4-일)피리딘-3-카르복사미드 + TX, 2-(디플루오로메틸)-N-(1,1-디메틸-3-프로필-인단-4-일)피리딘-3-카르복사미드 + TX, 2-(디플루오로메틸)-N-(3-이소부틸-1,1-디메틸-인단-4-일)피리딘-3-카르복사미드 + TX, 2-(디플루오로메틸)-N-[(3R)-1,1,3-트리메틸인단-4-일]피리딘-3-카르복사미드 + TX, 2-(디플루오로메틸)-N-[(3R)-3-에틸-1,1-디메틸-인단-4-일]피리딘-3-카르복사미드 + TX, 및 2-(디플루오로메틸)-N-[(3R)-1,1-디메틸-3-프로필-인단-4-일]피리딘-3-카르복사미드 + TX로 이루어진 군으로부터 선택된 생물학적 활성 화합물(여기서, 이러한 카르복사미드 화합물 각각은 WO 2014/095675호 및/또는 WO 2016/139189호에 기술된 절차에 따라 제조될 수 있다).

(Penpicoxamide [517875-34-2]) + TX (as described in WO 2003/035617), (1S)-2,2-bis(4-fluorophenyl)-1-methylethyl N -{[3-(acetyloxy)-4-methoxy-2-pyridyl]carbonyl}-L-alaninate [1961312-55-9] (Florylpicot as described in WO 2016/122802) SAMID) + TX, 2-(difluoromethyl)-N-(1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)- N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl -Indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3- Carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoro Romethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, and 2-(difluoromethyl)-N-[ Biologically active compounds selected from the group consisting of (3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide + TX, wherein each of these carboxamide compounds is WO 2014/ 095675 and/or WO 2016/139189).

Reference numbers in parentheses after the active ingredient, eg [3878-19-1] , refer to the chemical abstract registration number. The mixing partners described above are known. [The Pesticide Manual] [The Pesticide Manual-A World Compendium; Thirteenth Edition; Editor: CDS TomLin; The British Crop Protection Council], where the active ingredient is included, it is described by the entry number provided in the parentheses above for a particular compound. For example, the compound “abamectin” is described as entry number (1). When “[CCN]” is added for a particular compound above, the compound of interest is referred to as “Compendium of Pesticide Common Names”, which is accessible on the Internet [A. Wood; Compendium of Pesticide Common Names , Copyright ⓒ 1995-2004]. For example, the compound “acetoprole” is described at the internet address http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred to above by the so-called "common name", the relevant "ISO common name" or other "common name" used in individual cases. If the designation is not a "general name", the properties of the designation used instead are given in round brackets for the particular compound. In such cases, if the IUPAC name, IUPAC/chemical abstract name, "chemical name", "common name", "compound name" or "development code" is used, or one of such designations or "general name" is not used , "Alternative name" is used. "CAS registration number" means a chemical abstract registration number.

Compounds of formula (I) selected from compounds 1.a.01-1.a.32 to 1.z.01-1.z.32 described in Table 1, and compounds described in Table 2 below, and The active ingredient mixture of the active ingredient as such is preferably in a mixing ratio of 100:1 to 1:6000, especially 50:1 to 1:50, more particularly 20:1 to 1:20, even more particularly 10:1 to 1: 10, most particularly from 5:1 to 1:5, particularly preferably from 2:1 to 1:2, likewise preferably from 4:1 to 2:1, above all 1:1, or 5 :1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1 :5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1 :600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1 :3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. The mixing ratio is by weight.

The mixture as described above comprises applying a composition comprising the mixture described above to a pest or its environment, except for methods of treatment of the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body. It can be used in pest control methods.

Compounds of Formula I selected from one of the compounds 1.a.01-1.a.32 to 1.z.01-1.z.32 described in Table 1 and the compounds described in Table 2 (below), and above Mixtures comprising one or more active ingredients, for example, from separate formulations of a single active ingredient component, such as a "tank-mix", in the form of a single "ready-mix" It can be applied in a combined spray mixture made, and in a sequential manner, i.e., if one is applied after one over a reasonably short period of time, such as hours or days, the combined use of a single active ingredient. Compounds of formula (I) selected from compounds 1.a.01-1.a.32 to 1.z.01-1.z.32 described in Table 1 and compounds described in Table 2 (below), and as described above The order of applying the same active ingredient(s) is not essential for carrying out the invention.

In a preferred composition, a mixture of component (A) and component (B) is provided, wherein component (A) is a compound of formula I as described above, component (B) is benzobindiflupyr, Isopyrazam, pidiflumetofen, azoxystrobin, cedacic acid, diphenoconazole, prothioconazole, chlorotalonyl, fenpropidine, acibenzolar-S-methyl, ciprofonazole, ciprodinyl, pen Propimorph, propiconazole, hexaconazole, fenconazole, pyrifenox, fludioxonil, pyroquilon, tricyclazole, fluazinam, mandipropamide, mefentrifluconazole, metalaxyl, Metalaxyl-M, oxadixyl , florylpicoxamide , methyltetraprole , oxathiafiproline , paclobutrazol , sulfur, thiavendazole , Aspergillus Flavus NRRL 21882 (Afla-Guard) ®) and Bacillus subtilis strain Amyloliquefaciens strain FZB24 (Taegro®).

Preferably, component (A) is a compound of formula (I) as described above, and component (B) is benzobindiflupyr, pidiflumetofen, isopyrazam, cedaxane, diphenoconazole, ciproconazole , Propiconazole, azoxystrobin, metalaxyl-M, ciprodinyl, chlorothalonyl, oxathiapiproline, mandipropamide, tricyclazole, fluazinam, fludioxynyl, prothiocona Sol, mefentrifluconazole, florylpicoxamide, and methyltetraprole.

More specifically, component (A) is a compound selected from the group of compounds 1.a.01-1.a.32 to 1.z.01-1.z.32 described in Table 1 (below), Component (B) is benzobindiflupyr, pidiflumetofen, isopyrazam, cedaxane, diphenoconazole, ciproconazole, propiconazole, azoxystrobin, metalaxyl-M, ciprodinyl, chlorotalo Neil, oxathiapiproline, mandipropamide, tricyclazole, fluazinam, fludioxynyl, prothioconazole, mefentrifluconazole, florylpicoxamide, and methyltetraprole. Preferably, component (A) is a compound selected from the group described in Table 2 (below), i.e. compounds of formulas Ia19, Ic19, Ik19, Im19, In19, Io19 or Ir19, Component (B) is benzobindiflupyr, pidiflumetofen, isopyrazam, cedaxane, diphenoconazole, ciproconazole, propiconazole, azoxystrobin, metalaxyl-M, ciprodinyl, chlorotalo Neil, oxathiapiproline, mandipropamide, tricyclazole, fluazinam, fludioxynyl, prothioconazole, mefentrifluconazole, florylpicoxamide, and methyltetraprole.

The component (B) used in combination with the component (A) can improve the latter effect on fungi, and vice versa. Additionally, fungicidal compositions can be effective against a broader spectrum of fungal pathogens that, when used alone, can be combated with individual active ingredients. Generally, the weight ratio of component (A) to component (B) is 1000:1 to 1:1000, or 100:1 to 1:100, or 50:1 to 1:50, or 20:1 to 1: 40, or 20:1 to 1:20, or 15:1 to 1:30, or 12:1 to 1:25, or 10:1 to 1:20, or 5:1 to 1:15, or 3: 1 to 1:10, or 2:1 to 1:5. Otherwise, the weight ratio of component (A) to component (B) is 2:1 to 1:2, or 4:1 to 2:1, or 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. It is understood that such mixing ratios include, on the one hand, ratios by weight and on the other hand, molar ratios. Synergy between active ingredients can be observed.

In a preferred composition, the active ingredient mixtures of component (A) and component (B) as described above are benzovindiflupyr, isopyrazam, pidiflumetofen, azocystrobin, cedaxane, diphenoconazole, pro Thioconazole, chlorotalonyl, fenpropidine, acibenzolar-S-methyl, ciproconazole, ciprodinyl, fenpropimorph, propiconazole, hexaconazole, fenconazole, pyrifenox, fluor Rudioxonyl, pyroquilon, tricyclazole, fluazinam, mandipropamide, mefentrifluconazole, metalaxyl, metalaxyl-M, oxadixyl, florylpicoxamide, methyltetraprole, oxathiapi Proline, Paclobutrazol, Sulfur, Thiavendazole, Aspergillus Flabus NRRL 21882 (Afla-Guard®) and Bacillus subtilis variants It may comprise an additional active ingredient component (C) selected from one of the amyloliquefaciens strain FZB24 (Taegro®), wherein component (B) and component (C) are not the same active ingredient.

The composition comprises the active ingredient compounds of component (A), component (B) and component (C) 20:1:1, 1:20:1, 1:1:20, 10:1:1, 1: 10:1, 1:1:10, 5:1:1, 1:5:1, 1:1:5, 2:1:1, 1:2:1, 1:1:2 or 1:1: It can contain in the weight ratio selected from 1. Synergy between the active ingredients can be observed.

The composition of the present invention in any conventional form, for example twin packs, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment fluid concentrates (FS), seeds Treatment solution (LS), seed treatment water dispersible powder (WS), seed treatment capsule suspension (CF), seed treatment gel (GF), emulsifiable concentrate (EC), suspension concentrate (SC), Suspension (sus), capsule suspension (CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), micro-emulsions (ME) , Oil dispersion (OD), oil miscible fluid (OF), oil miscible fluid (OL), water soluble concentrate (SL), ultra low volume suspension (SU), ultra low volume liquid (UL), industrial concentrate ( TK), dispersible concentrates (DC), wettable powders (WP) or any technically viable formulations in combination with agriculturally acceptable adjuvants.

Such compositions are prepared in a conventional manner, for example, by incorporating the active ingredients into suitable formulation inerts (diluents, solvents, fillers and optionally other formulated ingredients such as surfactants, biocides, antifreeze agents, tackifiers, thickeners) And compounds that provide an adjuvancy effect). In addition, conventional sustained-release formulations can be used, in which long-lasting efficacy is intended. In particular, formulations to be applied in spray form, such as water-dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders and granules, surfactants and adjuvants such as wetting and dispersing agents Other compounds that provide an effect, such as formaldehyde and naphthalene sulfonates, alkylarylsulfonates, lignin sulfonates, fatty alkyl sulfates, and condensation products of ethoxylated alkylphenols and ethoxylated fatty alcohols.

In the form of a suitable seed powder formulation, for example, as an aqueous suspension with good adhesion to the seed or in the form of a dry powder, using the combination and diluent of the invention, the seed powder formulation is seed in a manner known per se. Applies to. Such seed meal formulations are known in the art. The seed meal formulation may contain single active ingredients, or may contain a combination of the active ingredients in encapsulated form, for example as a sustained release capsule or microcapsule.

In general, the formulation comprises 0.01 to 90% by weight of active agent, 0 to 20% by weight of agriculturally acceptable surfactant and 10 to 99.99% by weight of solid or liquid formulation inert material and adjuvant(s), wherein The active agent consists of at least a compound of the formula (I) together with component (B) and component (C), and optionally other active agents, in particular biocides or preservatives. The concentrated form of the composition generally contains about 2 to 80% by weight of active agent, preferably about 5 to 70% by weight. The application form of the formulation may contain, for example, 0.01 to 20% by weight of active agent, preferably 0.01 to 5% by weight. Commercial products will preferably be formulated as a concentrate, but the end user will typically use a diluted formulation.

Example

The following examples serve to illustrate the invention.

The compounds of the present invention can be distinguished from known compounds by greater efficacy at lower application rates, which, if necessary, lower application rates, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, Using 0.8 ppm or 0.2 ppm, it can be demonstrated by those skilled in the art using the experimental procedures outlined in the examples.

Compounds of formula (I) may have a number of benefits, which are particularly advantageous for use as an advantageous level of biologically active or agrochemically active ingredient to protect plants against diseases caused by fungi (eg For example, greater biological activity, favorable activity spectrum, increased safety profile (including improved crop resistance), improved physico-chemical properties, or increased biodegradability) are included.

List of abbreviations

℃ = Celsius degree

CDCl ₃ =chloroform-d

d = doublet

HATU = 1-[bis(dimethylamino)methylene]-1 H -1,2,3-triazolo[4,5- b ]pyridinium 3-oxide hexafluorophosphate

m = multiplet

MHz = megahertz

mp = melting point

ppm = parts per million

q = quartet

s = singlelet

t = triplet

Example 1 : This example is 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-car Preparation of copyimide (Compound 1.r.19) is illustrated:

a) Preparation of methyl 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylate

Xantphos (1.2 g, 2.0 mmol), tris (dibenzylideneacetone) dipalladium (0.9 g, 1.0 mmol), cesium carbonate (6.4 g, 19.7 mmol), and 4-amino-2,6 -Difluoropyridine (1.3 g, 9.9 mmol) was added sequentially to a mixture of methyl 2-bromo-5-methylthiazole-4-carboxylate (2.45 g, 9.9 mmol) in dioxane (350 mL) Did. The mixture was flushed with argon for 20 minutes and then heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel using ethyl acetate and cyclohexane as eluents to give methyl 2-[(2,6-difluoro-4-pyridyl)amino]- 5-Methyl-thiazole-4-carboxylate (1.0 g, 3.5 mmol) was calculated. ¹ H-NMR (400 MHz, CDCl ₃ ): d = 2.73 (s, 3H), 3.91 (s, 3H), 6.76 (s, 1H), 7.25 (s, 1H), 8.29 (bs, 1H).

b) Preparation of 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylic acid

Lithium hydroxide monohydrate (0.6 g, 25 mmol) methyl 2-[(2,6-difluoro-4-pyridyl)amino in a mixture of tetrahydrofuran (12 mL) and water (12 mL)] To a solution of -5-methyl-thiazole-4-carboxylate (1.8 g, 6.3 mmol). The reaction mixture was stirred at room temperature for 16 hours, after which the solvent was removed under reduced pressure. The residue was diluted with water, and then 2N hydrochloric acid was added slowly until a pH of 3-4 was reached. The resulting precipitate was filtered, washed with cold water and dried in a vacuum oven to give 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylic acid (0.9 g, 5.7 mmol). ¹ H-NMR (400 MHz, d ₆ -DMSO): d = 2.63 (s, 3H), 7.28 (s, 2H), 11.33 (bs, 1H), 12.91 (bs, 1H).

c) 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Compound 1. Preparation of r.19)

N,N-diisopropylethylamine (0.37 ml, 2.12 mmol), (2,2-dimethylcyclobutyl)ammonium chloride (0.14 g, 1.01 mmol) and HATU (0.39 g, 1.01 mmol) are N,N-dimethyl To a solution of 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxylic acid (0.25 g, 0.92 mmol) in formamide (9.2 mL) And the reaction mixture was stirred at room temperature for 40 minutes. Saturated sodium bicarbonate aqueous solution was added followed by water, and the solution was extracted twice with ethyl acetate. The phases were separated, and the organic layer was washed once with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using ethyl acetate and cyclohexane as eluents, and 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl Cyclobutyl)-5-methyl-thiazole-4-carboxamide (0.28 g, 0.79 mmol) was calculated. ¹ H-NMR (400 MHz, CDCl ₃ ): d = 1.17 (s, 3H), 1.20 (s, 3H), 1.50-1.75 (m, 2H), 1.86-1.92 (m, 1H), 2.29-2.36 ( m, 1H), 2.79 (s, 3H), 4.25-4.31 (m, 1H), 6.87 (s, 2H), 7.32 (d, 1H), 7.67 (s, 1H).

Table 1 below illustrates examples of individual compounds of formula I according to the present invention.

[Table 1]

Individual compounds of formula I according to the invention

here,

a) 32 compounds of formula I.a:

[Formula I.a]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

b) 32 compounds of formula I.b:

[Formula I.b]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

c) 32 compounds of formula I.c:

[Formula I.c]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

d) 32 compounds of formula I.d:

[Formula I.d]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

e) 32 compounds of formula I.e:

[Formula I.e]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

f) 32 compounds of formula I.f:

[Formula I.f]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

g) 32 compounds of formula I.g:

[Formula I.g]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

h) 32 compounds of formula I.h:

[Formula I.h]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

i) 32 compounds of formula I.i:

[Formula I.i]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

j) 32 compounds of formula I.j:

[Formula I.j]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

k) 32 compounds of formula I.k:

[Formula I.k]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

m) 32 compounds of formula I.m:

[Formula I.m]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

n) 32 compounds of formula I.n:

[Formula I.n]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

o) 32 compounds of formula I.o:

[Formula I.o]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

p) 32 compounds of formula I.p:

[Formula I.p]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

q) 32 compounds of formula I.q:

[Formula I.q]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

r) 32 compounds of formula I.r:

[Formula I.r]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

s) 32 compounds of formula I.s:

[Formula I.s]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

t) 32 compounds of formula I.t:

[Formula I.t]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

u) 32 compounds of formula I.u:

[Formula I.u]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

v) 32 compounds of formula I.v:

[Formula I.v]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

w) 32 compounds of formula I.w:

[Formula I.w]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

x) 32 compounds of formula I.x:

[Formula I.x]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

y) 32 compounds of formula I.y:

[Formula I.y]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

z) 32 compounds of formula I.z:

[Formula I.z]

Here, R ¹ , R ² , R ³ , R ⁴ and X are as defined in Table 1.

Throughout this specification, temperature is given in degrees Celsius (° C.) and “mp” means melting point. LC/MS stands for liquid chromatography mass spectrometry, and the description of the apparatus and method is as follows: (ACQUITY UPLC from Waters, Phenomenex Gemini C18, 3 μm particle size, 110 Angstrom, 30×3 mm column, 1.7 mL/min, 60°C, H ₂ O + 0.05% HCOOH (95%)/CH ₃ CN/MeOH 4:1 + 0.04% HCOOH (5%)-2 min-CH ₃ CN/MeOH 4:1 + 0.04% HCOOH (5%)-0.8 min, ACQUITY SQD mass spectrometer from Waters, ionization method: electrospray (ESI), polarity: cation, capillary (kV) 3.00, cone (V) 20.00, extractor (V) 3.00, source temperature (°C) 150, desolvation temperature (°C) 400, cone gas flow rate (L/Hr) 60, desolvation gas flow rate (L/Hr) 700)).

[Table 2]

Melting point and LC/MS data for selected compounds in Table 1 (R _t = Residence time)

Formulation Examples

The active ingredient is thoroughly mixed with the adjuvant, and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder, which can be diluted with water to provide a suspension at the desired concentration.

The active ingredient is thoroughly mixed with the adjuvant, and the mixture is thoroughly ground in a suitable mill to obtain a powder, which can be used directly for seed treatment.

This concentrate can be diluted with water to obtain an emulsion of any desired dilution rate that can be used for plant protection.

Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable mill. These powders can also be used in dry powder for seeds.

The active ingredient is mixed with the adjuvant and ground, and the mixture is humidified with water. The mixture is extruded and then dried in an air stream.

The finely ground active ingredient is uniformly applied in a mixer to kaolin humidified with polyethylene glycol. In this way, non-dusty coated granules are obtained.

The finely ground active ingredient can be intimately mixed with the adjuvant to provide a suspension concentrate, which can be diluted with water to obtain a suspension at any desired dilution rate. Using such dilutions, living plants as well as plant propagation materials can be treated and protected against invasion by microorganisms by spraying, injection or immersion.

The finely ground active ingredient can be intimately mixed with the adjuvant to provide a suspension concentrate, which can be diluted with water to obtain a suspension at any desired dilution rate. Using such dilutions, living plants as well as plant propagation materials can be treated and protected against invasion by microorganisms by spraying, injection or immersion.

Sustained release capsule suspension

28 parts of the combination of the compound of formula I is mixed with 2 parts of aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoam and 51.6 parts water until the desired particle size is achieved. To this emulsion, a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added. The mixture is stirred until the polymerization reaction is complete.

The obtained capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. Capsule suspension formulations contain 28% of the active ingredient. The median capsule diameter is 8 to 15 microns.

The resulting formulation is applied to seeds as an aqueous suspension in a device suitable for that purpose.

Biological examples

Blue Almeria gras mini bus differentiated species Tree Tea City (Blumeria graminis f. Sp. Tritici ) ( Erie Príncipe gras mini bus differentiated species Tree Tea City (Erysiphe graminis f. Sp. Tritici )) / wheat / leaf disc preventative (in wheat Powdery mildew)

Wheat leaf sections of the cultivar Kanzler (cv. Kanzler) are placed on agar in a multiwell plate (24 well format) and sprayed with test compounds formulated with DMSO and Tween20 and diluted in water. On the first day after application, leaf discs are inoculated by shaking powdery mildew-infected plants on a test plate. Inoculated leaf discs were incubated at 20° C. and 60% rh under a lighting scheme of 12 hour light/12 hour cancer after 24 hours of cancer in a climatic chamber and when appropriate levels of disease damage appeared on untreated control leaf sections ( 6-8 days after application), the activity of the compound is evaluated as% disease control rate compared to untreated.

Compounds I.a.19, I.c.19, and I.r.19 at 200 ppm in the formulation provide a disease control rate of at least 80% in this test compared to untreated control leaf discs (which indicate extensive disease development) under the same conditions.

Boat Riotinia Pucelliana ( Botryotinia fuckeliana )(Botrytis Cinerea( Botrytis cinerea )) / Liquid culture (gray mold)

The fungal conidia from cryogenic storage is mixed directly into the nutrient broth (Bogels broth). (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the addition of a nutrient broth containing fungal spores. The test plate is incubated at 24° C. and growth inhibition is determined by photometry 3 to 4 days after application.

200 ppm of compounds I.c.19 and I.r.19 in the formulation provide a disease control rate of at least 80% in this test against untreated control leaf discs (which exhibit extensive mycelial growth) under the same conditions.

Glomerella Ragenarium ( Glomerella lagenarium ) Colletotricum lagenarium( Colletotrichum lagenarium )) / Liquid culture (anthrax)

The fungal conidia from cryogenic storage is mixed directly into the nutrient broth (PDB potato dextrose broth). (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the addition of a nutrient broth containing fungal spores. The test plate is incubated at 24° C., and growth inhibition is measured by photometry 3 to 4 days after application.

200 ppm of compounds Ia19, Ic19, Io19 and Ir19 in the formulation provides at least 80% disease control rate in this test as compared to untreated control leaf discs (which indicate extensive disease development) under the same conditions. .

Magnaforte Grisea ( Magnaporthe grisea )(Piricularia orizai( Pyricularia oryzae )) / Rice / Leaf disc prevention (fever)

Rice leaf sections of the cultivar varilla (cv. Ballila) are placed on agar in a multiwell plate (24 well format) and sprayed with test compounds formulated with DMSO and Tween20 and diluted in water. On the second day after application, leaf sections are inoculated with a fungal spore suspension. Inoculated leaf sections were incubated at 22° C. and 80% rh under a lighting plan of 12 hour light/12 hour cancer after 24 hours of cancer in a climate cabinet, and when appropriate levels of disease damage appeared in untreated control leaf sections (apply) After 5-7 days), the activity of the compound is evaluated as% disease control rate compared to untreated.

Compounds I.a.19, I.c.19 and I.r.19 at 200 ppm in the formulation provide a disease control rate of at least 80% in this test as compared to untreated control leaf discs (which indicate extensive disease development) under the same conditions.

Monographella nivallis( Monographella nivalis ) (Microdocium nivale) / liquid culture (brown rot of cereals (foot rot))

The fungal conidia from cryogenic storage is mixed directly into the nutrient broth (PDB potato dextrose broth). (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the addition of a nutrient broth containing fungal spores. The test plate is incubated at 24° C., and growth inhibition is determined by photometry 4 to 5 days after application.

200 ppm of compounds Ia19, Im19, Io19 and Ir19 in the formulation provide at least 80% disease control rate in this test as compared to untreated control leaf discs (which exhibit extensive mycelial growth) under the same conditions. .

Mycospirella Arakidis ( Mycosphaerella arachidis )(Cercosfora Araki Dicola ( Cercospora arachidicola )) / Liquid culture (early leaf spot)

The fungal conidia from cryogenic storage is mixed directly into the nutrient broth (PDB potato dextrose broth). (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the addition of a nutrient broth containing fungal spores. The test plate is incubated at 24° C., and growth inhibition is determined by photometry 4 to 5 days after application.

200 ppm of compound I.r.19 in the formulation provides a disease control rate of at least 80% in this test as compared to untreated control leaf discs (which exhibit extensive mycelial growth) under the same conditions.

Mycospirella Gramini Cola ( Mycosphaerella graminicola )(Septoria Tritici( Septoria tritici )) / Liquid culture (Septoria half disease)

The fungal conidia from cryogenic storage is mixed directly into the nutrient broth (PDB potato dextrose broth). (DMSO) solution of the test compound is placed in a microtiter plate (96-well format), followed by the addition of a nutrient broth containing fungal spores. The test plate is incubated at 24° C., and growth inhibition is determined by photometry 4 to 5 days after application.

200 ppm of compounds Ia19, Ic19, Ik19, Io19 and Ir19 in the formulation are at least 80% disease control rate in this test compared to untreated control leaf discs (which exhibit extensive mycelial growth) under the same conditions. Gives

Paeospaeria no room (Septoria no room) Septoria nodorum )) / Wheat / Leaf Disc Preservative (Glume blotch)

Wheat leaf sections of cultivar Kanzler are placed on agar in a multiwell plate (24 well format) and sprayed with the formulated test compound diluted in water. On the second day after application, the leaf discs are inoculated with a fungal spore suspension. Inoculated test leaf discs are incubated at 20° C. and 75% rh under a lighting plan of 12 hour light/12 hour cancer in a climate cabinet, and when appropriate levels of disease damage appear in untreated control leaf discs (5-7 after application) Day 1) Evaluate the activity of the compound as% disease control rate compared to untreated.

200 ppm of compound I.r.19 in the formulation provides a disease control rate of at least 80% in this test as compared to untreated control leaf discs (which indicate extensive disease development) under the same conditions.

Puccinia Recondita Eruption Trinity( Puccinia recondita f. sp. tritici ) / Wheat / Leaf disc prevention (brown rust)

Wheat leaf sections of cultivar kansler are placed on agar in a multiwell plate (24 well format) and sprayed with the formulated test compound diluted in water. On the first day after application, the leaf discs are inoculated with a fungal spore suspension. Inoculated leaf sections were incubated at 19° C. and 75% rh under a 12 hour light/12 hour arm lighting scheme in a climate cabinet, and when appropriate levels of disease damage appeared in untreated control leaf sections (7-9 days post application) ), the activity of the compound is evaluated as% disease control rate compared to untreated.

Compounds I.a.19, I.c.19 and I.r.19 at 200 ppm in the formulation provide a disease control rate of at least 80% in this test as compared to untreated control leaf discs (which indicate extensive disease development) under the same conditions.

Claims (15)

A compound of formula (I): or a salt or N-oxide thereof:
[Formula I]

[In the above formula,
R ¹ is halogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ haloalkyl;
R ² is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl;
R ³ is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl;
R ⁴ is hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl, or C ₃ -C ₄ cycloalkyl;
R ⁵ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₆ haloalkenyl, C _2- C ₆ haloalkynyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moieties are nitrogen, oxygen and sulfur A 5 or 6 membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties, respectively, represented by R ⁷ Optionally substituted with 1 to 3 groups;
R ⁶ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₆ haloalkenyl, C _2- C ₆ haloalkynyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moieties are nitrogen, oxygen and sulfur A 5 or 6 membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties, respectively, represented by R ⁷ Optionally substituted with 1 to 3 groups;
R ⁷ is halogen, cyano, hydroxyl, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, or C ₃ -C ₄ cycloalkyl;
X is CH or N]. The compound of claim 1, wherein R ¹ is chloro, fluoro, bromo, methyl, ethyl or isopropyl. The compound according to claim 1 or 2, wherein R ² is hydrogen, methyl, ethyl, methoxy or ethoxy. The compound according to claim 1, wherein R ³ is halogen or C ₁ -C ₃ alkyl. The compound according to any of claims 1 to ⁴ , wherein R ⁴ is hydrogen, methyl, ethyl, methoxy or ethoxy. The method of claim 1, wherein R ⁵ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkynyl, C ₃ -C ₄ cycloalkyl, or phenyl, wherein: C ₃ -C ₄ cycloalkyl and phenyl moiety are each optionally substituted with 1 to 3 groups represented by R ⁷ . The method of claim 1, wherein R ⁶ is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cyclo. Alkyl, or phenyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur, C _3- C ₆ cycloalkyl, phenyl and heteroaryl moieties are optionally substituted with 1 to 3 groups represented by R ⁷ . The compound according to any one of claims 1 to ⁷ , wherein R ⁷ is halogen, C ₁ -C ₃ alkyl, or C ₁ -C ₃ alkoxy. 9. When R ⁵ is hydrogen or C ₁ -C ₃ alkyl, R ⁶ is C ₁ -C ₃ alkyl, phenyl, or thienyl, according to any one of claims 1 to 8, wherein phenyl and thi A compound wherein the nil moiety is optionally substituted with 1 or 2 groups selected from R ⁷ . The compound according to any one of claims 1 to 9, wherein X is N. The compound of formula (I) according to any one of claims 1 to 8, or 10, wherein 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-. (2-methylcyclobutyl)thiazole-4-carboxamide (1.c.19), 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2-ethylcyclo Butyl)-5-methyl-thiazole-4-carboxamide (1.d.19), N-(2,2-difluorocyclobutyl)-2-[(2,6-difluoro-4 -Pyridyl)amino]-5-methyl-thiazole-4-carboxamide (1.p.19), 2-[(2,6-difluoro-4-pyridyl)amino]-N-( 2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (1.r.19), or N-(2,2-diethylcyclobutyl)-2-[(2,6 -Difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxamide (1.s.19). A pesticide composition comprising a fungicidal effective amount of a compound of formula I according to claim 1. The composition of claim 12, further comprising at least one additional active ingredient and/or agrochemically acceptable diluent or carrier. A method for controlling or preventing the invasion of phytopathogenic microorganisms into useful plants, wherein the fungicidally effective amount of the compound of formula I according to any one of claims 1 to 11, or a composition comprising such a compound as an active ingredient, A method applied to a plant, to parts of it, or to its habitat. Use of a compound of formula (I) according to any one of claims 1 to 11 as a fungicide.